5. Chirality

Indicate whether each of the following structures is (R)-2-chlorobutane or (S)-2-chlorobutane:

c.

d.

Chloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each of its asymmetric centers?

What is the configuration of each of the asymmetric centers in the following compounds?

a.

b.

In Problem 5-3, you drew the enantiomers for a number of chiral compounds. Now go back and designate each asymmetric carbon atom as either (R) or (S).

(e) chlorocyclohexane

(f) cis-1,2-dichlorocyclobutane

Prioritize the substituents at each chiral center and then, by comparing them to the models you created in Section 6.3.2, label the absolute configuration as R or S.

(a)

Complete the structure of each of these so that it matches the (R) or (S) configuration associated with the name.

(e)

Of the following pairs, identify the higher priority substituent according to the CIP rules. (R = position of attachment to the asymmetric center.)

(a)

Using IUPAC rules, name the following molecules.

(c)

Using IUPAC rules, name the following molecules.

(d)

What is the configuration of the asymmetric centers in the following compounds?

a.

b.

Given the name, draw the structure of the following compounds.

(e) (3R,5S)-5-chloro-3-isopropylcycloheptene

Prioritize the substituents at each chiral center and then, by each of the two methods discussed in Section 6.3.2.4, determine the absolute configuration. [Do not use your models, except to check your answers.]

(h)

Name the following alkynes according to the IUPAC rules of nomenclature.

(c)