5. Chirality

From the IUPAC name, draw the corresponding structure.

(a) (R)-6-iodo-3-isopropylnon-1-ene

Star (*) each asymmetric carbon atom in the following examples, and determine whether it has the (R) or (S) configuration.

(i)

Given the following molecule: ${\mathrm{CH}}_3-\mathrm{CHBrClF}$, select the correct $R$ or $S$ configuration for the stereocenter carbon atom (the carbon bonded to Br, Cl, F, and H).

Naproxen is a commercially available anti-inflammatory sold under the name Aleve.

(a) Assign the absolute configuration as R or S.

Draw the structures that correspond to the following names.

(b) (3Z,8S)-8-ethyl-3-methylundec-3-en-6-yne

A student decided that the configuration of the asymmetric centers in a sugar such as D-glucose could be determined rapidly by simply assigning the R configuration to an symmetric center with an OH group on the right and the S configuration to an symmetric center with an OH group on the left. Is he correct?

Draw the structure that corresponds to the compound names shown.

(b) (5R,6E)-5-bromooct-6-en-1-yne

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.]

(d)

From the IUPAC name, draw the corresponding structure.

(b) (1R,2S)-1-chloro-2-methylcyclobutane

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

(d)

Given the following IUPAC names, draw the corresponding structures.

(a) (R)-3-isopropyl-6-methylnon-1-ene

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).

(c)

(d) 1-bromo-2-methylbutane

Given the following names, draw the structure of the molecule.

c. (S)-2-methyloctan-4-amine