5. Chirality

Identify

5. achiral compounds

6. meso compounds

7. enantiomers

8. diastereomers

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

e.

f.

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

c.

d.

Define the relationship between each set of two molecules as chain isomers, positional isomers, functional group isomers, enantiomers, diastereomers, conformational isomers, or identical

(d)

In Assessment 9.26, what is the relationship between the enantiomers of compound A and the enantiomers of compound B?

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

(d)

(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.

(b)

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

c.

d.

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

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

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)