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 of the stereocenters (circled) in Figure 5-5,

a. draw the compound with two of the groups on the stereocenter interchanged.

b. give the relationship of the new compound to the original compound.

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

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

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

(h)

Make a model and draw a three-dimensional structure for each compound. Then draw the mirror image of your original structure and determine whether the mirror image is the same compound. Label each structure as being chiral or achiral, and label pairs of enantiomers.

(e)

(f)

For the molecules shown,

(i) count the number of stereocenters present and

(ii) draw all possible stereoisomers.

(iii) Identify the relationships between stereoisomers as enantiomers or diastereomers.

(a)

(i) Which of the following pairs of compounds would you expect to have different physical properties?

(ii) What is the relationship between each of the pairs?

(iii) Assign the absolute configuration of each stereocenter to confirm your answer.

(a)