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Chapter 3: Problem 14

Which compounds contain chiral centers? (a) 2-Chloropentane (b) 3-Chloropentane (c) 3-Chloro-1-pentene (d) 1,2 -Dichloropropane

Short Answer

Expert verified
(a) 2-chloropentane, (b) 3-chloropentane, (c) 3-chloro-1-pentene, (d) 1,2-dichloropropane Answer: Compounds (a) 2-chloropentane and (b) 3-chloropentane contain chiral centers, while compounds (c) 3-chloro-1-pentene and (d) 1,2-dichloropropane do not.

Step by step solution

01

Draw the structure of 2-chloropentane

Draw the structure of 2-chloropentane as a five-carbon chain (pentane) with a chlorine atom substituting one hydrogen on the second carbon.
02

Analyze chiral centers in 2-chloropentane

The second carbon in 2-chloropentane has 4 different groups attached to it: a hydrogen, a chlorine, an ethyl group, and a propyl group. Therefore, the second carbon in the 2-chloropentane molecule is a chiral center.
03

Draw the structure of 3-chloropentane

Draw the structure of 3-chloropentane as a five-carbon chain (pentane) with a chlorine atom substituting one hydrogen on the third carbon.
04

Analyze chiral centers in 3-chloropentane

The third carbon in 3-chloropentane has 4 different groups attached to it: a hydrogen, a chlorine, an ethyl group, and a methyl group. Therefore, the third carbon in the 3-chloropentane molecule is also a chiral center.
05

Draw the structure of 3-chloro-1-pentene

Draw the structure of 3-chloro-1-pentene with a five-carbon chain and a double bond between the first and second carbons (1-pentene), and a chlorine atom substituting one hydrogen on the third carbon.
06

Analyze chiral centers in 3-chloro-1-pentene

The third carbon in 3-chloro-1-pentene has three different groups attached to it (a chlorine, hydrogen, and an ethyl group), and shares a double bond with the second carbon. Since there are only three unique groups, this carbon is not a chiral center.
07

Draw the structure of 1,2-dichloropropane

Draw the structure of 1,2-dichloropropane as a three-carbon chain (propane) with a chlorine atom replacing a hydrogen on both the first and second carbons.
08

Analyze chiral centers in 1,2-dichloropropane

The first carbon has a chlorine, a hydrogen, and a methyl group attached to it, while the second carbon has a chlorine, a hydrogen, and an ethyl group attached to it. There are only three unique groups on both the first and the second carbons, so neither of them are chiral centers.
09

Conclusion

Based on the analysis above, compounds (a) 2-chloropentane and (b) 3-chloropentane contain chiral centers, while compounds (c) 3-chloro-1-pentene and (d) 1,2-dichloropropane do not.

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Most popular questions from this chapter

One reason we can be sure that \(s p^{3}\)-hybridized carbon atoms are tetrahedral is the number of stereoisomers that can exist for different organic compounds. (a) How many stereoisomers are possible for \(\mathrm{CHCl}_{3}, \mathrm{CH}_{2} \mathrm{Cl}_{2}\), and \(\mathrm{CHClBrF}\) if the four bonds to carbon have a tetrahedral arrangement? (b) How many stereoisomers would be possible for each of these compounds if the four bonds to the carbon had a square planar geometry?

When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of \(\left[2-{ }^{14} \mathrm{C}\right]\) citric acid is formed stereoselectively. Note that citric acid containing only \({ }^{19} \mathrm{C}\) is achiral. Assign an \(R\) or \(S\) configuration to this enantiomer of \(\left[2{ }^{14} \mathrm{C}\right]\) citric acid. Note: Carbon- 14 has a higher priority than carbon-12.

Assign priorities to the groups in each set. (a) \(-\mathrm{H}-\mathrm{CH}_{3}-\mathrm{OH}-\mathrm{CH}_{2} \mathrm{OH}\) (b) \(-\mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}-\mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{COOH}\) (c) \(-\mathrm{CH}_{3}-\mathrm{H}-\mathrm{COO}^{-}-\mathrm{NH}_{3}{ }^{+}\) (d) \(-\mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{SH}-\mathrm{NH}_{3}^{+}-\mathrm{CHO}\)

How many stereoisomers exist for \(1,4-\) cyclohexanediol?

The chiral catalyst \((R)\)-BINAP-Ru is used to hydrogenate alkenes to give alkanes (Section \(6.7 \mathrm{C}\) ). The products are produced with high enantiomeric excess. An example is the formation of \((S)\)-naproxen, a pain reliever. (a) What kind of isomers are the enantiomers of BINAP? (b) How can one enantiomer of naproxen be formed in such high yield?
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