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(b) (+)-alanine. Both happen to have the S configuration, although one is levorotatory and the other is dextrorotatory.**
One additional point needs to be mentioned—the matter of **absolute configuration**. How do we know that the assignments of R and S configuration are correct in an absolute sense, rather than a re... | {
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**TABLE 5.2 Relationships among the Four Stereoisomers of Threonine**
| Stereoisomer<br>Enantiomer | | Diastereomer |
|----------------------------|-------|-----------------|
| 2R,3R | 2S,3S | 2R,3S and 2S,3R |
| 2S,3S | 2R,3R | 2R,3S and 2S,3R |
**TABLE 5.2 Rela... | {
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The most common method for resolving the racemate of a chiral carboxylic acid (RCO2H) is to carry out an acidbase reaction between the acid and an amine base (RNH2) to yield an ammonium salt:
To understand how this method of resolution works, let's see what happens when a racemic mixture of chiral acids, such as (+... | {
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(The "S" in the name <sup>S</sup>-adenosylmethionine stands for sulfur and means that the adenosyl group is attached to the sulfur atom of the amino acid methionine.) The molecule has S stereochemistry at sulfur and is configurationally stable for several days at room temperature. Its R enantiomer is also known but is ... | {
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$$H_3$$
C OH $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C $H_3$ C... | {
"Header 1": "WORKED EXAMPLE 5.2",
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$$H_3$$
C $H_3$ C $H_4$ C $H_5$ C $H_5$ C $H_6$ C $H_7$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $H_8$ C $... | {
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As just one example, the conversion of citrate to cis-aconitate in the citric acid cycle has been shown to occur with loss of a pro-R hydrogen, implying that the OH and H groups leave from opposite sides of the molecule.
$$\begin{array}{cccccccccccccccccccccccccccccccccccc$$
**[PROBLEM](#page-454-10)** Identify the... | {
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#### **Chiral Drugs**
The many hundreds of different pharmaceutical agents approved for use by the U.S. Food and Drug Administration come from many sources. Many drugs are isolated directly from plants or bacteria, and others are made by chemical modification of naturally occurring compounds. An estimated 33%, howeve... | {
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Which are chiral?
- **PROBLEM** Draw compounds that fit the following descriptions:
- **5-35 (a)** A chiral alcohol with four carbons **(b)** A chiral carboxylic acid with the formula C5H10O<sup>2</sup>
#### **(c)** A compound with two chirality centers **(d)** A chiral aldehyde with the formula C3H5BrO
**PROBLEM 5... | {
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**5-48**
**PROBLEM** Assign R or S stereochemistry to the chirality centers in the following Newman projections:
5-49 (a)
$$CI$$
(b) $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ $H_3C$ ... | {
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Because it is much less prone to cause tooth decay than sucrose, xylose has been used in candy and chewing gum. Assign R or S configurations to the chirality centers in xylose.
#### **Meso Compounds**
**PROBLEM** Draw examples of the following:
> **5-51 (a)** A meso compound with the formula C8H<sup>18</sup> **(b... | {
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For example, the reaction of sodium acetylide with 2-butanone yields 3-methyl-1-pentyn-3-ol:
$$\begin{array}{c|c}
O & & & \\
H_3C & & & \\
\hline
C & & & \\
C & & & \\
C & & & \\
C & & & \\
C & & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
C & & \\
... | {
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**FIGURE 6.1 Many chemical reactions are like pole vaulters going over the bar.** They need a big, initial push of activation energy. (credit: "UChicago Pole Vault" by Eric Guo/Flickr, CC BY 2.0)
#### **CHAPTER CONTENTS**
- **[6.1 Kinds of Organic Reactions](#page-183-0)**
- **[6.2 H... | {
"Header 1": "An Overview of Organic Reactions",
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Bond polarity is a consequence of an unsymmetrical electron distribution in a bond and is due to the difference in electronegativity of the bonded atoms.
Elements such as oxygen, nitrogen, fluorine, and chlorine are more electronegative than carbon, so a carbon atom bonded to one of these atoms has a partial positive... | {
"Header 1": "An Overview of Organic Reactions",
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Let's begin by looking at the two reactants.
What do we know about ethylene? We know from Section 1.8 that a carbon–carbon double bond results from the orbital overlap of two $sp^2$ -hybridized carbon atoms. The $\sigma$ part of the double bond results from $sp^2-sp^2$ overlap, and the $\pi$ part results from ... | {
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**The electrophilic addition reaction of ethylene and HBr.** The reaction takes place in two steps, both of which involve electrophile–nucleophile interactions.
When one of the alkene carbon atoms bonds to the incoming hydrogen, the other carbon atom, having lost its share of the doubl... | {
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$$\begin{array}{cccccccccccccccccccccccccccccccccccc$$
As a biological example of a radical reaction, look at the synthesis of prostaglandins, a large class of molecules found in virtually all body tissues and fluids. A number of pharmaceuticals are based on or derived from prostaglandins, including medicines that ... | {
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For example, if a reaction breaks reactant bonds with a total strength of 380 kJ/mol and forms product bonds with a total strength of 400 kJ/mol, then ΔH for the reaction is 400 kJ/mol – 380 kJ/mol = −20 kJ/mol and the reaction is exothermic.
The **entropy change (ΔS)** is a measure of the change in the amount of mol... | {
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Sometimes, particularly in biochemistry, reactive substances that undergo highly exothermic reactions, such as ATP (adenosine triphosphate), are referred to as "energy-rich" or "high-energy" compounds. Such a label doesn't mean that ATP is special or different from other compounds, it only means that ATP has relative... | {
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If the collision has occurred with enough force and proper orientation, however, the reactants continue to approach each other despite the rising repulsion until the new C–H bond starts to form. At some point, a structure of maximum energy is reached, a structure called the **transition state**.
The transition state ... | {
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#### **Strategy**
A two-step reaction has two transition states and an intermediate between them. The ΔG ‡ for the overall reaction is the energy change between reactants and the highest-energy transition state—the second one in this case. An exergonic reaction has a negative overall ΔG°.
#### **Solution**
![](... | {
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#### **Where Do Drugs Come From?**
It has been estimated that major pharmaceutical companies in the United States spent some \$200 billion on drug research and development in 2020, while government agencies and private foundations spent another \$28 billion. What does this money buy? From 1983 to 2022, the money resu... | {
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**PROBLEM 6-16** Electrostatic potential maps of **(a)** formaldehyde (CH2O) and **(b)** methanethiol (CH3SH) are shown. Is the formaldehyde carbon atom likely to be electrophilic or nucleophilic? What about the
**PROBLEM** Look at the following energy... | {
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+ \bigcirc$ $\longrightarrow$
#### **Polar Reactions**
#### **PROBLEM** Identify the functional groups in the following molecules, and show the polarity of each:
6-29 (a)
$$CH_3CH_2C \equiv N$$
(b) $OCH_3$ (c) $OCH_3$ (d) $CH_3CCH_2COCH_3$ (e) $OCH_3$ (f) $OCH_3$ (f) $OCH_3$ (c) $OCH_3$ (d) $OCH_... | {
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(a)
$$\underset{N_3}{\ominus}$$
+ $\underset{CH_3Cl}{CH_3N_3}$ + $\underset{Cl}{\ominus}$ (b) $\underset{NO_2}{\bigoplus}$ + $\underset{NO_2}{\bigoplus}$
**(c)**
**PROBLEM** Add curved arrows to the following polar reactions to indicate the flow of electrons in each:
6-33 (a)
$$\begin{array}{c} H \\ H \e... | {
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Explain.
- **PROBLEM 6-36** Despite the limitations of radical chlorination of alkanes, the reaction is still useful for synthesizing certain halogenated compounds. For which of the following compounds does radical chlorination give a single monochloro product?
(a)
$$CH_3CH_3$$
(b) $CH_3CH_2CH_3$ (c) $CH_3$ (d) ... | {
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What is the value of ΔG° (in kJ/mol) at 298 K? Is the reaction exothermic or endothermic? Is it exergonic or endergonic?
**PROBLEM 6-43** Methoxide ion (CH3O − ) reacts with bromoethane in a single step according to the following equation:
$$CH_3\overset{..}{\overset{..}{\circ}} + H_{\overset{..}{\overset{..}{\circ... | {
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**PROBLEM 6-46** Predict the product(s) of each of the following biological reactions by interpreting the flow of electrons as indicated by the curved arrows:
(a)
$$H_3C$$
(b) $H_3C$ $OPO_3^{2-}$ $POP_1$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_2$ $POP_... | {
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**FIGURE 7.1 Tomatoes are good for you**. Their red color is due to lycopene, which has 13 double bonds. (credit: "Tomatoes" by Jeremy Keith/Flickr, CC BY 2.0)
#### **CHAPTER CONTENTS**
- **[7.1 Industrial Preparation and Use of Alkenes](#page-219-0)**
- **[7.2 Calculating the Degree... | {
"Header 1": "Alkenes: Structure and Reactivity",
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**[PROBLEM](#page-456-1)** Calculate the degree of unsaturation in each of the following formulas, and then draw as many
- **7-1** structures as you can for each:
- **[\(a\)](#page-456-1)** C4H<sup>8</sup> **[\(b\)](#page-456-1)** C4H<sup>6</sup> **[\(c\)](#page-456-1)** C3H<sup>4</sup>
**[PROBLEM](#page-456-2)**... | {
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| TABLE 7.1 Common Names of Some Alkenes | | |
|----------------------------------------|------------------------|-------------|
| Compound | Systematic name | Common name |
| | Ethene | Ethy... | {
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For rotation to occur around a double bond, the $\pi$ bond must break and re-form (FIGURE 7.3). Thus, the barrier to double-bond rotation must be at least as great as the strength of the $\pi$ bond itself, an estimated 350 kJ/mol (84 kcal/mol). Recall that the barrier to bond rotation in ethane is only 12 kJ/mol. ... | {
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**[PROBLEM](#page-456-13)** Which member in each of the following sets ranks higher?
**7-11 [\(a\)](#page-456-13)** −H or −CH<sup>3</sup> **[\(b\)](#page-456-13)** −Cl or −CH2Cl **[\(c\)](#page-456-13)** –CH2CH2Br or –CH CH<sup>2</sup> **[\(d\)](#page-456-13)** −NHCH<sup>3</sup> or −OCH<sup>3</sup> **[\(e\)](#page-... | {
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If we interconvert cis-2-butene with trans-2-butene and allow them to reach equilibrium, we find that they aren't of equal stability. The trans isomer is more stable than the cis isomer by 2.8 kJ/mol (0.66 kcal/mol) at room temperature, corresponding to a 76 : 24 ratio.
$$\begin{array}{cccc}
H_{3}C & CH_{3} & \stackr... | {
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| | | ΔH°hydrog | |
|------------------|------------------|----------------------|-------------------------|
| Substitution | Alkene | (kJ/mol) | (kcal/mol) |
| Ethylene | | −136 ... | {
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2-Methylpropene 2-Chloro-2-methylpropane (94%)
$$CH_{3} = C - CH_{3} - C - CH_{3}$$
$$CH_{3} = C - CH_{3} - C - CH_{3}$$
$$CH_{3} = C - CH_{3} - C - CH_{3}$$
$$CH_{3} = C - CH_{3} - C - CH_{3}$$
$$CH_{3} = C - CH_{3} - C - CH_{3}$$
$$CH_{3} = C - CH_{3} - C - CH_{3}$$
$$CH_{3} = C - CH_{3} - C - CH_{3}$... | {
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Solvent
$$C = CH_2 + HCl \xrightarrow{Ether} CH_3 - C - Cl$$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$
$CH_3 - C - Cl$... | {
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Reactant
$$H_3C$$
$C=CH_2$
$H_3C$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$CH_3$
$C... | {
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Why should this be?
#### **Predicting the Product of an Electrophilic Addition Reaction**
What product would you expect from reaction of HCl with 1-ethylcyclopentene?
#### **Strategy**
When solving a problem that asks you to predict a reaction product, begin by looking at the func... | {
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$$\begin{array}{cccccccccccccccccccccccccccccccccccc$$
**PROBLEM** Predict the products of the following reactions:
7-16 (a) (b)
$$CH_3$$
(c) $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_4$ $CH_5$ $CH_5$ $CH_5$ $CH_5$ $CH_5$ $CH_5$ $CH_5$ $CH_5$ ... | {
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**FIGURE 7.10 The structure of a carbocation**. The trivalent carbon is sp 2 -hybridized and has a vacant p orbital perpendicular to the plane of the carbon and three attached groups.
The second point to explore involves carbocation stability. 2-Methylpropene might react with H<sup>+... | {
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Conversely, the transition state for an exergonic reaction (**[FIGURE 7.15](#page-240-1)**b), is closer energetically, and thus structurally, to the reactant than to the product. We therefore say that the transition state for an exergonic reaction step structurally resembles the reactant for that step.
#### **Hammond... | {
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How do we know that the carbocation mechanism for electrophilic addition reactions of alkenes is correct? The answer is that we *don't* know it's correct; at least we don't know with complete certainty. Although an incorrect reaction mechanism can be disproved by demonstrating that it doesn't account for observed data,... | {
"Header 1": "7.11 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements",
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$$\begin{array}{c} \text{H}_{3}\text{C} \\ \text{H}_{3}\text{C} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{H} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{H} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{H} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{C} \\ \text{H} \\ \text{Shift... | {
"Header 1": "7.11 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements",
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#### **Bioprospecting: Hunting for Natural Products**
Most people know the names of the common classes of biomolecules—proteins, carbohydrates, lipids, and nucleic acids—but there are many more kinds of compounds in living organisms than just those four. All living organisms also contain a vast diversity of substance... | {
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Add curved arrows to show the mechanism of each step. Which step involves an alkene electrophilic addition? (The ion OP2O6 4− is the diphosphate ion, and "Base" is an unspecified base in the enzyme that catalyzes the reaction.)
$$\begin{array}{cccccccccccccccccccccccccccccccccccc$$
**PROBLEM 7-33** epi-Aristolochen... | {
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#### **Alkene Isomers and Their Stability**
**PROBLEM** Rank the following sets of substituents according to the Cahn–Ingold–Prelog sequence rules:
**7-45 (a) (b) (c)**
(d)
$$\bigcirc \\ -\text{CH}_3, -\text{CH}_2\text{CH}_3, -\text{CH}_2\text{CH}_2\text{OH}, -\text{CCH}_3$$
(e) $-\text{CH}=\text{CH}_2, -\text... | {
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**7-48 (a) (b) (c)**
**PROBLEM 7-49** trans-2-Butene is more stable than cis-2-butene by only 4 kJ/mol, but trans-2,2,5,5-tetramethyl-3-hexene is more stable than its cis isomer by 39 kJ/mol. Explain.
**PROBLEM 7-50** Cyclodecene can exist in both cis and trans forms, but cyclohexene cannot. Explain.
**PROBLEM ... | {
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$$\begin{array}{ccc} & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ & & & \\ ... | {
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**FIGURE 8.1 The Spectra fiber used to make the bulletproof vests used by police and military is made of ultra-high-molecular-weight polyethylene, a simple alkene polymer.** (credit: modification of work "US Navy 081028-N-3857R-007 Seabees participate in a chemical, biological and radiol... | {
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$$\begin{array}{c} H \\ C = C \\ H \end{array} \begin{array}{c} H \\ C = C \\ H \end{array} \begin{array}{c} C C C C \\ C C \\ C C \\ C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\ C C C \\... | {
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#### **8.3 Halohydrins from Alkenes: Addition of HO-X**
Another example of an electrophilic addition is the reaction an alkene with either Br2 or Cl2 in the presence of
water to yield a 1,2-halo alcohol, called a **halohydrin**.
$$C = C \qquad \frac{X_2}{H_2O} \qquad C - C \qquad + HX$$
We saw in the previous... | {
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**[PROBLEM](#page-457-13)** What products would you expect from oxymercuration–demercuration of the following alkenes?
8-7 (a)
$$_{\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}=\text{CH}_2}$$
(b) $_{\text{CH}_3}$ $_{\text{CH}_3\text{C}=\text{CHCH}_2\text{CH}_3}$
**PROBLEM** From what alkenes might the following a... | {
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In organic chemistry, however, a **reduction** is a reaction that results in a gain of electron density for carbon, caused either by bond formation between carbon and a less electronegative atom—usually hydrogen—or by bond-breaking between carbon and a more electronegative atom—usually oxygen, nitrogen, or a halogen. W... | {
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Complete hydrogenation yields the corresponding saturated fatty acids, but incomplete hydrogenation often results in partial cis–trans isomerization of a remaining double bond. When eaten and digested, the free trans fatty acids are released, raising blood cholesterol levels and potentially contributing to coronary pro... | {
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This nucleophilic addition is analogous to the final step of alkene bromination, in which a cyclic bromonium ion is opened by a nucleophile (**[Section 8.2](#page-256-0)**). That is, a trans-1,2-diol results when an epoxycycloalkane is opened by aqueous acid, just as a trans-1,2-dibromide results when a cycloalkene is ... | {
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$$C = C \qquad \begin{array}{c} O_3 \\ \hline C = C \end{array} \qquad \begin{array}{c} O_3 \\ \hline C = C \end{array} \qquad \begin{array}{c} O_3 \\ \hline C = C \end{array} \qquad \begin{array}{c} O_3 \\ \hline C = C \end{array} \qquad \begin{array}{c} O_3 \\ \hline C = C \end{array} \qquad \begin{array}{c} O_3 \\... | {
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Instead, the ozonide is immediately treated with a reducing agent, such as zinc metal in acetic acid, to produce carbonyl compounds. The net result of the ozonolysis/reduction sequence is that the bond is cleaved and an oxygen atom becomes doubly bonded to each of the original alkene carbons. If an alkene with a tetras... | {
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#### **Predicting the Reactant in an Ozonolysis Reaction**
What alkene would yield a mixture of cyclopentanone and propanal on treatment with ozone followed by reduction with zinc?
?
$$\frac{1.0_3}{2. \text{ Zn, acetic acid}}$$
$0$ + $CH_3CH_2CH$
#### **Strategy**
Reaction of an alkene with ozone, followed by... | {
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$$\begin{array}{c} \mathsf{CH}_2\mathsf{OH} \\ \mathsf{HO} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \mathsf{OH} \\ \... | {
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The simplest synthetic polymers are those that result when an alkene is treated with a small amount of a suitable catalyst. Ethylene, for example, yields polyethylene, an enormous alkane that may have a molecular weight up to 6 million u and may contain as many as 200,000 monomer units. Worldwide production of polyethy... | {
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$$\begin{array}{cccccccccccccccccccccccccccccccccccc$$
$$C = C \qquad \xrightarrow{\text{Rad}} \qquad \begin{bmatrix} \text{Rad} & & \\ -C - C & \end{bmatrix} \qquad \xrightarrow{C = C} \qquad \xrightarrow{\text{Rad}} \qquad C = C \qquad \xrightarrow{C - C - C} \qquad \xrightarrow{C = C} \qquad \xrightarrow{C - C -... | {
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Only one substrate molecule at a time is present in the active site of an enzyme, and that molecule is held in a precise position, with other necessary reacting groups nearby. As a result, biological radical reactions are more controlled and more common than laboratory or industrial radical reactions. A particularly im... | {
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Fee
$$O_2H$$
$O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ $O_2H$ ... | {
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#### **8.12 Reaction Stereochemistry: Addition of H2O to an Achiral Alkene**
Most of the biochemical reactions that take place in the body, as well as many organic reactions in the laboratory, yield products with chirality centers. For example, acid-catalyzed addition of H2O to 1-butene in the laboratory yields 2-b... | {
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$$\begin{bmatrix}
H & 0 & H \\
0 & \delta^{+} \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3}CH_{2} & C & H \\
CH_{3... | {
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$$\begin{array}{c} Re \\ \hline -O_2C \\ \hline -O_2C \\ \hline \end{array}$$
$$\begin{array}{c} C \\ \hline \\ C \\ \hline \end{array}$$
$$\begin{array}{c} C \\ \hline \\ C \\ \hline \end{array}$$
$$\begin{array}{c} C \\ \hline \\ C \\ \hline \end{array}$$
$$\begin{array}{c} C \\ \hline \\ C \\ \hline \end{a... | {
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What would happen, though, if we were to carry out the reaction on a single enantiomer of a chiral reactant? For example, what stereochemical result would be obtained from addition of H2O to a chiral alkene, such as (R)-4-methyl-1-hexene? The product of the reaction, 4-methyl-2-hexanol, has two chirality centers and so... | {
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#### **Terpenes: Naturally Occurring Alkenes**
Ever since its discovery in Persia around 1000 A.D., it has been known that steam distillation, the distillation of plant materials together with water, produces a fragrant mixture of liquids called essential oils. The resulting oils have long been used as medicines, spi... | {
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\text{ Hg(OAc)}_2, \text{ H}_2\text{O/THF}} \qquad \qquad C - C$$
e. Addition of water by hydroboration–oxidation (**[Section 8.5](#page-263-0)**) Non-Markovnikov syn addition occurs.
$$> C = C < \xrightarrow{1. BH_3, THF} C - C$$
f. Catalytic hydrogenation (**[Section 8.6](#page-266-0)**) Syn addition occurs.
... | {
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Cleavage of 1,2-diols (**[Section 8.8](#page-272-0)**)
$$\begin{array}{c} \begin{array}{c} \begin{array}{c} \begin{array}{c} \begin{array}{c} \begin{array}{c} \\ \end{array} \end{array} \\ \begin{array}{c} \\ \end{array} \end{array} \\ \begin{array}{c} \\ \end{array} \\ \begin{array}{c} \\ \end{array} \\ \begin{array... | {
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Tell in each case whether you would use hydroboration–oxidation or oxymercuration–demercuration.
**PROBLEM 8-24** The following alkene undergoes hydroboration–oxidation to yield a single product rather than a mixture. Explain the result, and draw the product showing its stereochemistr... | {
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$$\begin{array}{c} \text{CH}_3 \\ \text{CH}_3 \\ \text{CH}_3 \text{C} = \text{CHCH}_2 \text{CH}_3 \\ \textbf{2-Methyl-2-pentene} \end{array} \begin{array}{c} \begin{array}{c} \text{H}_3 \text{C} \quad \text{OH} \\ \hline \textbf{1.} \quad \text{BH}_3, \text{THF, 25 °C} \\ \hline \textbf{2.} \quad \text{H}_2 \text{O}_... | {
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cis-CH<sub>3</sub>CH=CHCH<sub>3</sub>
$$\xrightarrow{\text{CH}_2I_2, Zn(Cu)}$$
?
trans-CH<sub>3</sub>CH=CHCH<sub>3</sub> $\xrightarrow{\text{CH}_2I_2, Zn(Cu)}$ ?
**PROBLEM 8-46** Predict the products of the following reactions. Don't worry about the size of the molecule; concentrate on the functional groups.
... | {
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(a)
$$CH_3$$
$CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ ... | {
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The following structure represents a segment of a copolymer called Saran. What two monomers were copolymerized to make Saran?
#### **General Problems**
- **PROBLEM 8-56** Compound A has the formula C10H16. On catalytic hydrogenation over palladium, it reacts with only 1 molar equivalent of H2. Compound **A** also u... | {
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**FIGURE 9.1 Synthesizing organic compounds is like conducting a musical group.** When in tune, chemists can create highly complex organic compounds. (credit: modification of work "Jazz great visits Navy" by U.S. Navy, Michael Worner/Wikimedia Commons, Public Domain)
#### **CHAPTER CON... | {
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The length of the bond is 120 pm, and its strength is approximately 965 kJ/mol (231 kcal/mol), making it the shortest and strongest known carbon–carbon bond.
**FIGURE 9.2 The structure of acetylene, . The bond angles are 180°, and the bond length is 120 pm.** The electrostatic potentia... | {
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$$R-C \equiv C-R' \xrightarrow{H_3O^+} \left( \begin{array}{c} \\ \\ \\ \\ \\ \end{array} \right) \left( \begin{array}{c} \\ \\ \\ \\ \end{array} \right) \left( \begin{array}{c} \\ \\ \\ \\ \end{array} \right) \left( \begin{array}{c} \\ \\ \\ \\ \end{array} \right) \left( \begin{array}{c} \\ \\ \\ \\ \end{array} \rig... | {
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Hydroboration–oxidation of an internal alkyne such as 3-hexyne is straightforward and gives a ketone, but hydroboration–oxidation of a terminal alkyne is more complex because two molecules of borane often add to the triple bond, complicating the situation. To prevent this double addition, a bulky, sterically encumbered... | {
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$$R-C \equiv \stackrel{\checkmark}{C-H} + \stackrel{.}{:} \stackrel{.}{N}H_2 Na^+ \longrightarrow R-C \equiv C:-Na^+ + :NH_3$$
According to the Brønsted–Lowry definition (**[Section 2.7](#page-59-0)**), an acid is a substance that donates H<sup>+</sup> . Although we usually think of oxyacids (H2SO4, HNO3) or haloge... | {
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Planning a synthesis makes you approach a chemical problem in a logical way, draw on your knowledge of chemical reactions, and organize that knowledge into a workable plan—it helps you learn organic chemistry.
There's no secret to planning an organic synthesis: all it takes is a knowledge of the different reactions a... | {
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$$\begin{array}{ccc} \text{CH}_3\text{CH}_2\text{CH}_2\text{C} \equiv \text{CCH}_3 & \xrightarrow{\text{H}_2} & \text{CH}_3\text{CH}_2\text{CH}_2 & \text{CH}_3\text{CH}_2\text{CH}_2 & \text{CH}_3\text{CH}_2\text{CH}_2 & \text{CH}_3\text{CH}_2\text{CH}_2 & \text{CH}_3\text{CH}_2\text{CH}_2 & \text{CH}_3\text{CH}_2\tex... | {
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$$CH_3CH_2CH_2C \equiv CH \xrightarrow{H_2} CH_3CH_2CH = CH_2$$
What is an immediate precursor of a terminal alkyne? Perhaps sodium acetylide and an alkyl halide.
$$Na^+: \overline{C} \equiv CH + BrCH_2CH_2CH_3 \longrightarrow CH_3CH_2CH_2C \equiv CH_3CH_2CH_2C \equiv CH_3CH_2CH_2C \equiv CH_3CH_2CH_2C \equiv CH_... | {
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CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>Br, THF
1-Pentyne
1-Pentyne
CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH=CH<sub>2</sub>
Lindlar catalyst
1-Pentene
$$\downarrow$$
HBr, ether
CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH=CH<sub>2</sub>
$\downarrow$ CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH=CH<sub... | {
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H}_2\text{O}_2, \text{NaOH} \end{array} } \begin{array}{c} \text{CH}_3 \\ \mid \\ \text{CH}_3\text{CHCH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text{CH}_2\text... | {
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\text{ NaNH}_2}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $\xrightarrow{\text{CH}_3}$ $... | {
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#### **The Art of Organic Synthesis**
**FIGURE 9.8** Vitamin B12 has been synthesized from scratch in the laboratory, but the bacteria growing on sludge from municipal sewage plants do a much better job. (credit: "Aeration and sludge-wasting" by U.S. Department of Agriculture/Flickr, P... | {
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Conversion into acetylide anions (**[Section 9.7](#page-309-0)**)
$$R-C\equiv C-H$$
$\xrightarrow{NaNH_2}$ $R-C\equiv C:-Na^+$ + $NH_3$
#### **Additional Problems**
#### **Visualizing Chemistry**
**PROBLEM 9-14** Name the following alkynes, and predict the products of their reaction with **(1)** H2 in the p... | {
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(a)
$$CH_2 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarrow CH_3 \longrightarr... | {
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$$\begin{array}{cccccccccccccccccccccccccccccccccccc$$
#### **Naming Alkynes**
**PROBLEM** Give IUPAC names for the following compounds:
9-26 (a)
$$CH_3$$
(b) $CH_3C \equiv CCH_2C \equiv CCH_2CH_3$ (c) $CH_3 CH_3$ $CH_3$ $CH_3CH_2C \equiv CCCH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $C... | {
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To what reaction of alkenes is the process analogous?
**PROBLEM** Predict the products of the following reactions:
**9-30**
$$\begin{array}{c|c}
H & H_2, Pd/C \\
C & C & H
\end{array}$$
$$\begin{array}{c|c}
H_2, Pd/C & A?
\end{array}$$
$$\begin{array}{c|c}
H_2/Lindlar & B?
\end{array}$$
**PROBLEM** Predict ... | {
"Header 1": "CHEMISTRY MATTERS",
"token_count": 2912,
"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
} |
$$\begin{array}{c|ccccccccccccccccccccccccccccccccccc$$
**PROBLEM** How would you carry out the following reactions?
**9-37 (a) (b)**
**(c)**
(d)
$$C \equiv CCH_3$$
$$C = CCH_3$$
$$CH_3CH_2C \equiv CH$$
$$CH_3CH_2C \equiv CH$$
$$CH_3CH_2C \equiv CH$$
(f)
$$CH_3CH_2CH_2CH=CH_2 \xrightarrow{?} CH_3CH_... | {
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(a)
$$_{\text{CH}_3\text{CH}_2\text{C} \equiv \text{CH}}$$
(b) $_{\text{CH}_3\text{CH}_2\text{C} \equiv \text{CCH}_2\text{CH}_3}$ (c) $_{\text{CH}_3}$ $_{\text{CH}_3\text{CHCH}_2\text{CH} = \text{CH}_2}$
(d)
$$_{0}$$
(e) $_{\mathrm{CH_{3}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}CH_{2}... | {
"Header 1": "CHEMISTRY MATTERS",
"token_count": 2036,
"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
} |
There is no one-step method for doing an alkene inversion, but the transformation can be carried out by combining several reactions in the proper sequence. How would you carry out the following reactions?
(a)
$$trans$$
-5-Decene $cis$ -5-Decene $cis$ -5-Decene $trans$ -5-Decene
**PROBLEM 9-50** Organometallic re... | {
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"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
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**FIGURE 10.1 The gases released during volcanic eruptions contain large amounts of organohalides, including chloromethane, chloroform, dichlorodifluoromethane, and many others.** (credit: "Tavurvur volcano" by Taro Taylor, Richard Bartz/Wikimedia Commons, CC BY 2.0)
#### **CHAPTER CON... | {
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"Header 2": "CHAPTER 10 Organohalides",
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"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
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**FIGURE 10.2 Mechanism of the radical chlorination of methane.** Three kinds of steps are required in radical substitution reactions: initiation, propagation, and termination. The propagation steps are a repeating cycle, with Cl**·** a reactant in step 1 and a product in step 2, and w... | {
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"token_count": 1962,
"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
} |
Which, if any, are chiral?
**[PROBLEM](#page-459-20) 10-4** Taking the relative reactivities of 1°, 2°, and 3° hydrogen atoms into account, what product(s) would you expect to obtain from monochlorination of 2-methylbutane? What would the approximate percentage of each product be? (Don't forget to take into account t... | {
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Each of the two allylic radicals can add a Br atom at either end (**A** or **A′**; **B** or **B′**), to give a mixture of up to four products. Draw and name the products. In the present instance, the "two" products from reaction at position **B** are identical, so only three products are formed in this reaction.
####... | {
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"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
} |
(a)
$$CH_3$$
(b) $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH_3$ $CH... | {
"Header 1": "CHEMISTRY MATTERS",
"Header 2": "CHAPTER 10 Organohalides",
"token_count": 2023,
"source_pdf": "datasets/websources/biochem/OrganicChemistry-SAMPLE_9ADraVJ.pdf"
} |
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