5. Chirality

Provide the full name for the following molecule, taking stereochemistry into account.

Provide the full name for the following molecule, taking stereochemistry into account.

Provide the full name for the following molecule, taking stereochemistry into account.

Given the following IUPAC names, draw the corresponding structures.

(c) (S)-3-fluoropent-1-ene

Draw the structures that correspond to the following names.

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

By comparing them to the models you created in Section 6.3.2, label the following chiral centers as R or S.

(j) <IMAGE>

Order the following sets of substituents via their priority using the CIP rules. ( of attachment to the asymmetric center.)

(a) <IMAGE>

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

(a) <IMAGE>

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) <IMAGE>

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.]

(c) <IMAGE>

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) <IMAGE>

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) <IMAGE>

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

(a) <IMAGE>

Draw the structure that corresponds to the name provided.

(c) (2E,4S,6Z)-octa-2,6-dien-4-ol

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

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

(••) Given the name, draw the structure of the following compounds.

(b) (4Z,8R)-8-bromo-5-methylnon-4-ene

(••) Given the name, draw the structure of the following compounds.

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

(•) Using IUPAC rules, name the following molecules.

(c) <IMAGE>

(•) Using IUPAC rules, name the following molecules.

(e) <IMAGE>

(•) Name the following alkynes according to the IUPAC rules of nomenclature.

(b) <IMAGE>

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

(d) <IMAGE>

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

(e) <IMAGE>

(•) Name the following alkynes according to the IUPAC rules of nomenclature.

(d) <IMAGE>

(•••) LOOKING AHEAD In Chapter 12, we introduce the S_N 2 reaction, a nucleophilic substitution reaction that proceeds with inversion. Confirm that inversion has occurred in each of the following examples by determining the absolute configuration of the chiral center in the reactants and products.

(a) <IMAGE>

(••) Assign the absolute stereochemistry for each of the following molecules.

(e) <IMAGE>

(••) Assign the absolute stereochemistry for each of the following molecules.

(f) <IMAGE>

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.

(d) <IMAGE>

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.

(f) <IMAGE>

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

c. <IMAGE>

Name the four stereoisomers of 1,3-dichloro-2-pentanol

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

<IMAGE>

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

a. <IMAGE> b. <IMAGE>

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

i. <IMAGE>

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

a. <IMAGE>

b. <IMAGE>

Name the following:

a.<IMAGE>

b. <IMAGE>

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?

<IMAGE>

What is the configuration of the following compounds? (Use the given structures to answer the question.)

a. <IMAGE>

b. <IMAGE>

What is the configuration of the following compounds? (Use the given structures to answer the question.)

c. <IMAGE>

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

a. <IMAGE>

b. <IMAGE>

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

c. <IMAGE>

d. <IMAGE>

What is the configuration about each of the asymmetric centers in aspartame?

Draw a perspective formula for each of the following:

a. (S)-3-chloro-1-pentanol

b. (2R,3R)-2,3-dibromopentane