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In 5-3, you drew the enantiomers for a number of chiral

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 7P Chapter 5

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 7P

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

Step-by-Step Solution:
Step 1 of 3

Solution 7P

Rules to assign the R and S configuration to the compounds is as follows:

1. First select the chiral center, and give the priority to the groups around the symmetric carbon atom (chiral carbon).

2. If the priority of the groups from highest to lowest is in clockwise direction, then the chiral center has R configuration.

3. If the priority of the groups from highest to lowest is in anti-clockwise direction, then the chiral center has S configuration.

4. The lowest priority group must be in below the plane (i.e. represented with dashed line).

(a)

The given compound is pentan-2-ol. Pentan-2-ol has one asymmetric carbon atom. It is indicated with blue colour.

Calculate the number of stereoisomers by using the following formula

Number of stereoisomers =

Here, n is number of asymmetric carbon atoms.

So, the number of stereoisomers for the compound pentan-2-ol is = 2 stereoisomers .

The two stereoisomers of pentan-2-ol are as follows:

The two stereoisomers are mirror images of each other. So, the two isomers are enantiomers.

Now, assign the R and S configuration to the two stereoisomers is as follows:

Thus, the two enantiomers of pentan-2-ol with R and S configuration are shown below:

(b)

The given compound is pentan-3-ol. Pentan-3-ol has no asymmetric carbon atoms.

Thus, the compound is pentan-3-ol is achiral.

(c)

The given compound is alanine. Alanine has one symmetric carbon. This is indicated with blue colour.

So, the number of stereoisomers for the compound alanine is = 2 stereoisomers ..

The two stereoisomers of alanine are shown below:

The two stereoisomers are mirror images of each other. So, the two isomers are enantiomers.

Now, assign the R and S configuration to the two stereoisomers is as follows:

Thus, the two enantiomers of alanine with R and S configuration are shown below:

(d)

The given compound is 1-bromo-2-methylbutane.

1-bromo-2-methylbutane has one asymmetric...

Step 2 of 3

Chapter 5, Problem 7P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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In 5-3, you drew the enantiomers for a number of chiral