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

Are the following pairs identical, enantiomers, diastereomers, or constitutional isomers?

c.

d.

Do the following structures represent identical compounds or a pair of enantiomers?

What type of isomerism is indicated by each of the following pairs of molecules? Be as specific as possible.

(a)

Identify

1. constitutional isomers

2. stereoisomers

3. cis–trans isomers

4. chiral compounds

Draw the mirror image of the following molecule. Then, using the mirror image generated, switch the spatial orientation at the asymmetric center. Is the final structure the enantiomer of the original? If not, what is it?

For each pair, give the relationship between the two compounds. Making models will be helpful.

(h)