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Chapter 5: Problem 88

Draw and specify as \(R\) or \(S\) the enantiomers of: (a) 3 -chloro-1-pentene (b) 3-chloro-4-methy1-1-pentene (c) HOOCCH \(_{2}\) CHOHCOOH, malic acid (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{NH}_{2}\)

Short Answer

Expert verified
The enantiomers of the given compounds are as follows: (a) 3-chloro-1-pentene: R-enantiomer (H on the top, Cl on the bottom); S-enantiomer (H on the bottom, Cl on the top) (b) 3-chloro-4-methyl-1-pentene: R-enantiomer (H on the top, Cl on the bottom, CH\(_3\) on the right); S-enantiomer (H on the bottom, Cl on the top, CH\(_3\) on the right) (c) Malic acid: R-enantiomer (hydrogen on the bottom, hydroxyl group on the right); S-enantiomer (hydroxyl group on the bottom, hydrogen on the right) (d) C\(_6\)H\(_5\)CH(CH\(_3\))NH\(_2\): R-enantiomer (C\(_6\)H\(_5\) on the left, CH\(_3\) on the top); S-enantiomer (C\(_6\)H\(_5\) on the left, CH\(_3\) on the bottom)

Step by step solution

01

(a) Draw the structure of 3-chloro-1-pentene

First, draw a pentene molecule, which is a 5-carbon chain with a double bond between the first and second carbons. Then, add the chlorine atom to the third carbon in the chain. The structure will look like this: ``` H H - C = C - C - C - H H | H Cl ```
02

(a) Identify the chiral center and draw enantiomers of 3-chloro-1-pentene

The carbon at position 3 has four different substituents (a hydrogen, a chlorine, and two different carbon chains). This makes it a chiral center. Draw the enantiomers as R and S. R-enantiomer: The Fischer projection will be as follows: ``` C=C | Cl-C-H | H ``` S-enantiomer: The Fischer projection will be as follows: ``` C=C | H-C-Cl | H ```
03

(b) Draw the structure of 3-chloro-4-methyl-1-pentene

First, draw a pentene molecule. Then, add the chlorine atom to the third carbon and a methyl group to the fourth carbon in the chain. The structure will look like this: ``` H H - C = C - C - C - H H | | H Cl CH_3 ```
04

(b) Identify the chiral center and draw enantiomers of 3-chloro-4-methyl-1-pentene

The carbon at position 3 has four different substituents (hydrogen, chlorine, methyl, and ethene), making it a chiral center. Draw the enantiomers as R and S. R-enantiomer: ``` C=C | Cl-C-CH_3 | H ``` S-enantiomer: ``` C=C | H-C-CH_3 | Cl ```
05

(c) Draw the structure of HOOCCH\(_{2}\)CHOHCOOH (malic acid)

The structure of malic acid is: ``` HOOC-CH_2-CHOH-COOH ```
06

(c) Identify chiral center and draw enantiomers of malic acid

The carbon at the third position has four different substituents (H, OH, CH\(_{2}\)COOH and COOH), making it a chiral center. Draw the enantiomers as R and S. R-enantiomer: ``` HOOC-CH_2-C | COOH | OH | H ``` S-enantiomer: ``` HOOC-CH_2-C | COOH | H | OH ```
07

(d) Draw the structure of C\(_{6}\)H\(_{5}\)CH(CH\(_{3}\))NH \(_{2}\)

The structure is: ``` NH_2 | C_6H_5 - CH - CH_3 ```
08

(d) Identify the chiral center and draw enantiomers of C\(_{6}\)H\(_{5}\)CH(CH\(_{3}\))NH\(_{2}\)

The carbon in the middle has four different substituents (C\(_{6}\)H\(_{5}\), CH\(_{3}\), NH\(_{2}\), and H), making it a chiral center. Draw the enantiomers as R and S. R-enantiomer: ``` C_6H_5 - C | | CH_3 NH_2 ``` S-enantiomer: ``` C_6H_5 - C | | NH_2 CH_3 ```

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Most popular questions from this chapter

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