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Chapter 20: Q38P (page 1075)

When pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:

(a)Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetric carbon atom. (Using your models may be helpful.)

(b)Determine the relationship between the two stereoisomers you have drawn.

Short Answer

Expert verified

a)

Three dimensional structures of the stereoisomers

(b) The relationship between the two isomers drawn is that they are diastereomers.

Step by step solution

01

About lactic acid

The organic compound that bears one carboxylic acid, one OH group, and three carbons in the parent chain is lactic acid. The IUPAC name for this compound is 2-hydroxypropanoic acid.

02

About butan-2-ol

The organic compound that bears four carbons in the parent chain and an OH at the second carbon is butan-2-ol.This compound is alcohol.

03

About the reaction

The lactic acid and butan-2-ol combine in the presence of an acid leading to the formation of 2-butyl lactate. In this compound, the lactic acid and butan-2-ol molecules join by a carbonyl group.

04

About the reaction

There will be the formation of two compounds which is a racemic mixture that is R and S. The reaction is shown below.

Chemical reaction

The two drawn isomers are diastereomers.

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Most popular questions from this chapter

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Question. (A true story.) The chemistry department custodian was cleaning the organic lab when an unmarked bottle fell off a shelf and smashed on the floor, leaving a puddle of volatile liquid. The custodian began to wipe up the puddle, but he was overcome with burning in his eyes and a feeling of having an electric drill thrust up his nose. He left the room and called the fire department, who used breathing equipment to go in and clean up the chemical. Three students were asked to identify the chemical quickly so that the custodian could be treated and chemical could be handled properly. The students took IR and NMR spectra, which follow. The UV spectrum showedat 220 nm(E= 16,000). The mass spectrometer was down, so no molecular weight was available. Determine the structure of this nasty compound, and show how your structure fits the spectra.

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Acetals can serve as protecting groups for 1,2-diols,as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called as acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

(a) The isoelectric point (pI) of phenylalanine is pH 5.5. Draw the structure of the major form of phenylalanine at pH values of 1,5.5, and 11.

(b) The isoelectric point of histidine is pH 7.6. Draw the structures of the major forms of histidine at pH values of 1, 4, 7.6, and 11. Explain why the nitrogen in the histidine ring is a weaker base than the伪 -amino group.

(c) The isoelectric point of glutamic acid is pH 3.2. Draw the structures of the major forms of glutamic acid at pH values of 1, 3.2, 7, and 11. Explain why the side-chain carboxylic acid is a weaker acid than the acid group next to the-carbon atom.
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