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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] attached to a carbon that has three other carbons attached to it [Question]
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tertiary alcohol
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] the hydrogen in the OH group is positively charged and is attracted to the lone pair of electrons on the negatively polarized oxygen atom of another molecule [Question]
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alcohols and phenols have much higher boiling points than similar alkanes and alkyl halides because
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] sp3 hybridized [Question]
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the strucure around O of the alcohol or phenol is similar to that in water, being that it is
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] present in solution(this accounts for the higher boiling point) but absent in the gas phase [Question]
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the molecular forces that make the boiling points of alcohols and phenols higher are present and absent when?
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Lewis Base and may be protonated by strong acids to yield oxonium ions, ROH2+ [Question]
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The oxygen lone pair in the OH group of alcohols and phenols can act as a
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] they can transfer a proton to water to a very small extent, and this creates a Hydrogen bonding network. Thus, alcohols are quite soluble in protic solvents. They can also react with bases, creating H30+ and an alkoxide ion RO-; or a phenoxide ion ArO- [Question]
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Alcohols can also be acidic by
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] increase the pKa of phenols [Question]
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The electron donating substituents that activate the ring toward electrophilic substitution also
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] decrease the pKa of phenols [Question]
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The electron withdrawing substituents that deactivate the ring
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] strengthening [Question]
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electron withdrawing groups are acid ___
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] weakening [Question]
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electron donating groups are acid ___
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] steric effects [Question]
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solvation and proton transfer can be affected by
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] more its formation is energetically favored [Question]
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the more easy an alkoxide ion is solvated, the
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] resonance stabilization of the phenoxide ion. Phenols react with NaOH solutions (but alcohols do not), forming salts that are soluble in dilute aqueous solution. [Question]
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Phenols are much more acidic than alcohols due to
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] extraction into basic aqueous solution and is isolated after acid is added to the solution [Question]
|
A phenolic compound can be separated from an organic solution by
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] of the resonance stabilization of the alkoxide anion. [Question]
|
Phenols with nitro groups at the ortho and para positions are much stronger acids because
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] -SO3R & -CO2R [Question]
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What other groups besides nitro can stabilize the alkoxide anion?
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] regiospecific(limited) but not stereospecific [Question]
|
hydration:
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] syn, non-Markovnikov hydration [Question]
|
hydroboration/oxidation:
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Markovnikov hydration [Question]
|
oxymercuration/reduction:
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] an alcohol [Question]
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Reduction of a carbonyl compound generally yields:
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Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] primary alcohols [Question]
|
reduction of aldehydes gives
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Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] secondary alcohols [Question]
|
reduction of ketones gives
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] sensitive to moisture and does not reduce other common functional groups. Adds the equivalent of "H" [Question]
|
NaBH4 is not
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[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] more powerful than NaBH4, less specific, and very reactive with water. Adds the equivalent of "H" [Question]
|
LiAlH4 is
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] primary alcohols(NaBH4 is not effective) [Question]
|
Carboxylic acids and esters are reduced using LiAlH4 to give
|
[] |
Flashcards about orgoexam2
|
Question
|
http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Grignard Reagents. These Grignard reagents in turn react with carbonyl compounds to yield alcohols [Question]
|
Alkyl, aryl, and vinylic halides react with Mg in ether or tetrahydrofuran to generate
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] nucleophilic carbanions in adding to the carbonyl group. The intermediate alkoxide is then protonated to produce the alcohol [Question]
|
Grignard Reagents act as
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[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] other stronger oxidizing agents will oxidize the intermediate aldehydes into carboxylic acids [Question]
|
to produce only an aldehyde, milder oxidizing agents must be used (PCC, C5H6NCrO3Cl) pyridium chlorochromate in dichloromethane bc
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] present in living systems [Question]
|
oxidizing agents used by chemists, such as chromate and permanganate salts are not
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a ketone as the product [Question]
|
oxidation of a secondary alcohol produces
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] sensitive secondary alcohols at low temperatures [Question]
|
PCC is used to oxidize
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] DMSO not an Aqueous solvent,so the product stops at the aldehyde. also, the reaction does not involve chromium-based reagents which are toxic [Question]
|
Swern Oxidiztion is carried out in
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] SN1 through carbocation intermediate to form alkyl halides [Question]
|
tertiary alcohols react with HCl or HBr by
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] SOCl2 or PBr3 via SN2 mechanism [Question]
|
primary and secondary alcohols are converted into halides by treatment with
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
|
[Answer] alkyl tosylates, ROTs. The formation of the tosylate does not involve the C–O bond so configuration at a chirality center is maintained. Alkyl tosylates react like alkyl halides, i.e. good leaving groups. [Question]
|
Reacting an alcohol with p-toluenesulfonyl chloride (tosyl chloride, p-TsCl)in pyridine yields
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] an inversion at the chirality center. [Question]
|
The SN2 reaction of an alcohol via a tosylate produces
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] two inversions, giving the product the same arrangement as the starting alcohol [Question]
|
The SN2 reaction of an alcohol via a halide proceeds with
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a dehydration reaction to create a pi bond. specific reagents are needed to facilitate this elimination (usually strong acid) [Question]
|
an alkene can be formed from an alcohol by
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] dehydrated with acid [Question]
|
tertiary alcohols are readily
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] severe conditions (75% H2SO4, 100C) and sensitive molecules dont survive [Question]
|
secondary alcohols require what for dehydration?
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] very harsh conditions; they are impractical and usually rearrange to form a more stable carbocation. reactivity is the resul of the nature of the carbocation intermediate [Question]
|
primary alcohols require what for dehydration?
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] dehydration of secondary and tertiary alcohols at low temperatures. This reaction proceeds via an E2 mechanism from an intermediate ester of POCl2 [Question]
|
Phosphorus oxychloride in the amine solvent pyridine can lead to
|
[] |
Flashcards about orgoexam2
|
Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] transfer their proton to a basic reagent [Question]
|
hydroxyl groups can easily
|
[] |
Flashcards about orgoexam2
|
Question
|
http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] protects the alcohol [Question]
|
Converting the hydroxyl to a (eventually removable) functional group without an acidic proton
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] an unreactive trimethylsilyl (TMS) ether. The ether can be cleaved with acid or with fluoride ion to regenerate the alcohol. [Question]
|
Reaction with chlorotrimethylsilane in the presence of base yields
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] good substrates for electrophilic halogenation, nitration, sulfonation, and Friedel–Crafts reactions (or any electrophilic substitution). [Question]
|
The hydroxyl group of phenols is strongly activating, making phenols
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a quinone [Question]
|
Reaction of a phenol with a strong oxidizing agent will yield
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a radical mechanism [Question]
|
Fremy's salt [(KSO3 )2 NO] works under mild conditions through
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] their redux reactions [Question]
|
Ubiquinones mediate electron-transfer processes involved in energy production through
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] has two organic groups (alkyl, aryl or vinyl) bonded to the same oxygen atom R-O-R' [Question]
|
Ether
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[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] sulfuric acid catalyzed dehydration of ethanol or other primary alcohols. This is a good way to prepare symmetrical ethers [Question]
|
diethyl ether can be prepared by
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] reaction of metal alkoxides and primary alkyl halides and tosylates. Best method for the preparation of ethers.Best way to prepare unsymmetrical ethers, but is a good way to prepare symmetrical ethers too [Question]
|
Williamson Ether Synthesis
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a strong base like NaH [Question]
|
Alkoxides made by reacting an alcohol with
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] ether in one step. Glucose reacts with excess iodomethane in the presence of Ag2O to generate a pentaether in 85% yield [Question]
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Reaction of alcohols with Ag2O directly with alkyl halide forms
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] react alkene with an alcohol and mercuric acetate or trifluoroacetate. demercuration with NaBH4 yields an ether. overall Markovnikov addition of alcohol to alkene. [Question]
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Alkoxymercuration of Alkenes
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] the hydration of an alkene [Question]
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Mechanicallistically, the alkoxymercuration of alkenes is analagous to
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] ethers are generally unreactive. strong acid will cleave an ether at elevated temperature. HI, HBr produce an alkyl halide from less hindered component by SN2(tertiary ethers undergo SN1) [Question]
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reactions of ethers: acidic cleavage
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a good leaving group (ROH) has been generated. [Question]
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The protonated ether can undergo substitution reactions because
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] it has a very poor leaving group (RO-) [Question]
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The neutral ether is unreactive because
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] they can dissolve both polar and non-polar organics and because they are unreactive with most reagents except strong acids. [Question]
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chemically inert ethers are commonly used as organic solvents because
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] the formation of explosive hydroperoxides [Question]
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autoxidation is an unwanted side reaction that makes the handling of some ethers potentially dangerous due to
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] cleavage occurs by an SN2 mechanism. Initial attack occurs on the less hindered carbon. The alcohol formed in the first step of the reaction will react further with HX. reaction is slow and requires high temperatures and concentrated acids [Question]
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Cleavage of Ethers by HX: primary and methyl ethers
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] The cleavage occurs by an SN1 mechanism with formation of the more stable carbocation. the reaction occurs at lower temperatures so the alcohol formed during the first step may not react further. E1 elimination will complete the substitution process. [Question]
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Cleavage of secondary, tertiary, allylic and benzylic ethers
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Autoxidation is a particular problem for 2° ethers but also occurs with common laboratory solvents such as diethyl ether and THF. [Question]
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Autoxidation of ethers
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] specific to allyl aryl ethers, ArOCH2CH=CH2. heating to 200-250C leads to an o-allylphenol. result is alkylation of the phenol in an ortho position [Question]
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Reactions of ethers: claisen rearrangement
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] the ring is 3-membered [Question]
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Cyclic ethers behave like acyclic ethers except if
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] solvents [Question]
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dioxane and tetrahydrofuran are used as
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] three membered ring ether is called an oxirane or an epoxide. [Question]
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Cyclic ethers: epoxides (oxiranes)
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] a reaction of ethylene with oxygen at 300C and silver oxide catalyst [Question]
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ethylene oxide is industrially important as an intermediate fro several processes. it is prepared by
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] 5 and 6 membered rings such as THF and THP are as unreactive as their acyclic analogues. [Question]
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reactions of cyclic ethers
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Any reaction that cleaves the ring releases about 25 kcal/mol of bond strain. This can make otherwise endergonic reactions thermodynamically feasible; can speedup the rate of reactions [Question]
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3 membered rings are uniquely reactive, much like cyclopropanes are much more reactive than ordinary alkanes. the reason for the reactivity is the same in both cases:
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] much more reactive than an acyclic ether [Question]
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the release of strain energy makes an epoxide
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Addition of HO-X to an alkene gives a halohydrin. Treatment of a halohydrin with base gives an epoxide via intermolecular willamson ether synthesis. The nucleophile and leaving group muct be able to be anti [Question]
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Epoxides from halohydrins
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] treat an alkene with a peroxyacid, mCPBA is the most common [Question]
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Preparation of Epoxides using a Peroxyacid
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] water adds to epoxides with dilute acid at room temperature to give a 1,2-diol. Mechanism: acid protonates oxygen and water adds to the opposite side(trans addition) [Question]
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Reactions of epoxides: acid catalyzed Ring-opening
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] anhydrous HF,HBr, HCl, or HI combines with an epoxide and gives a trans product [Question]
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halohydrins from epoxides
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Nucleophile preferably adds to less hindered site if primary and secondary C’s. Beware however, if there is a tertiary center the ring will open to generate the tertiary carbocation and the nucleophile will add there. [Question]
|
regiochemistry of acid-catalyzed opening of epoxides
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] The stereoselectivity is consistent with an ordinary SN 2 reaction, but the regiochemistry is not. [Question]
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rapid acid catalyzed ring cleavage of epoxides
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] The transition state for the reaction has an unbalanced structure with bond cleavage ahead of bond formation. [Question]
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the transition state for an epoxide opening
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Epoxides are subject to SN 2 reactions under conditions in which other ethers are inert. The attack occurs at the less hindered carbon and with inversion of configuration at the reacting carbon. [Question]
|
nucleophilic addition (and ring opening) TO EPOXIDES
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] strain of the three membered ring is relieved on ring opening. hydroxide cleaves epoxides at elevated temperatures to give trans 1,2-diols [Question]
|
base catlayzed epoxide opening: SN2
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] reactions with nucleophilic organo metallics RLi and RMgX are important C-C bond forming reactions. The configuration of the carbon that does not react remains unchanged [Question]
|
organometallic addition to epoxides
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] arene oxides are subject to two different reactions, the first is the nucleophilic attack like other epoxides and the second is a rearrangement via the NIH shift to make phenols [Question]
|
epoxides in biological systems: arene oxides
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] nucleophilic sites on the DNA bases, particularly deoxyguanosine [Question]
|
chemical carcinogens are electrophiles that react with
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] specifically bind certain metal ions or organic molecules to form a host-guest complex, an example of molecular recognition. [Question]
|
crown ethers
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] are not normally soluble in. The anions that are brought into solution are very weakly solvated. these weakly solvated anions may react at an increased rate in these solvents as nucleophiles, redox reagents etc. [Question]
|
crown ethers can serve as phase-transfer catalysts by bringing ionic salts into non-polar solvents that they
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] thiols (RSH) named with the suffix thiol. SH group is called a mercapto group [Question]
|
thiols are sulfure analogs of alcohols
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] In protic solvents RS- are better nucleophiles than the corresponding RO- because they are less heavily solvated. [Question]
|
although they have similar chemistry to alcohols, thiols have unique properties that are distinct from alcohols
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] H2S is not as good a leaving group as H2O and RSH is more difficult to protonate. [Question]
|
RSH2+ are not usually used as substrates in substitution reactions because
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Flashcards about orgoexam2
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] From alkyl halides by displacement with a sulfur nucleophile such as –SH or S-2 . The alkylthiol product can undergo further reaction with the alkyl halide to give a symmetrical sulfide, giving a poorer yield of the thiol. [Question]
|
thiols: formation and reaction
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Thioamides may be hydrolyzed to yield thiols, but very slow and relatively basic conditions are necessary. [Question]
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thiols: formation and reaction 2
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Thiols can undergo further reaction with the alkyl halide to give dialkyl sulfides. For a pure alkylthiol use thiourea (NH2 (C=S)NH2 ) as the nucleophile. [Question]
|
using thiourea to form alkylthiols
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] This gives an intermediate alkylisothiourea salt, which is hydrolyzed cleanly to the alkyl thiourea. [Question]
|
using thiourea to form alkylthiols 2
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Reaction of an alkyl thiol (RSH) with bromine or iodine gives a disulfide (RSSR). The thiol is oxidized in the process and the halogen is reduced. [Question]
|
oxidation of thiols to disulfates
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Thiolates (RS- ) are formed by the reaction of a thiol with a base. Thiolates react with primary or secondary alkyl halide to give sulfides (RSR’). Thiolates are excellent nucleophiles and react with many electrophiles. [Question]
|
sulfides
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Reaction is analogous to the Williamson ether synthesis. Since RS- is a relatively weak base it is less likely to cause elimination reactions than is RO- . R' should still be as unhindered as possible. [Question]
|
More on the Synthesis of Thioethers (Sulfides).
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] nucleophilic than an ether is [Question]
|
The thioether is far more
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] The 3p electrons valence electrons (on S) are less tightly held than 2p electrons (on O). Sulfides react with primary alkyl halides (SN 2) to give trialkylsulfonium salts (R3 S+ ) [Question]
|
Sulfur compounds are more nucleophilic than their oxygen-compound analogs.
|
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Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Sulfides are easily oxidized with H2O2 to the sulfoxide (R2 SO). Oxidation of a sulfoxide with a peroxyacid yields a sulfone (R2 SO2 ). Dimethyl sulfoxide (DMSO) is often used as a polar aprotic solvent. [Question]
|
oxidation reactions of sulfides/thioethers
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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d0e645f0_Flashcards_about_orgoexam2__Question
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[Answer] Aldehydes (RCHO) and ketones (R2 CO) are characterized by the the carbonyl functional group (C=O) The compounds occur widely in nature as intermediates in metabolism and biosynthesis [Question]
|
Aldehydes and Ketones
|
[] |
Flashcards about orgoexam2
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Question
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http://www.studystack.com/flashcard-873938
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16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
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