Star (*) each asymmetric carbon atom in the following

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

Problem 6P 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 6P

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

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Solution 6P

Chirality center: An atom (usually carbon) which is bonded to four different atoms or groups is known as chiral center.

R and S configuration can be assign to the compound by using the following CIP (Cahn-Ingold-Prelog) sequence rules:

Rule 1: Select the chiral center in the compound and assign priorities to the atoms based on its atomic number. The atom which is having highest atomic number gets the first priority and atom which is having least atomic number (usually hydrogen) fourth priority.

Rule 2: If the isotopes of same atom are attached to the chiral center, then the atom with the higher atomic mass receives higher priority.

Rule 3: If the first atom of each substituent is same then give priority to the second atom in the each substituent. This process in continue to the third and fourth until the rule difference is reached.

Rule 4: If the substituents have multiple bonds, the multiple bonded atoms are considered as same number of single bond

If the rotation of the numbering is in clockwise direction, then the configuration of the isomer is R. Similarly, if the rotation of the numbering is in anticlockwise direction, then the configuration of the isomer is S.

(a)

The asymmetric carbon atom is represented with an asterisk as follows:

The priority order of the groups is: The hydroxyl group receives first priority, the (-CH2CH3) group second priority, the methyl group third, and the hydrogen is fourth.

The rotation is in anticlockwise direction, so the configuration would be S, but the least priority group is in above the plane. Thus, the configuration would be reversed.

Therefore, the configuration of this compound is represented as follows:

(b)

The asymmetric carbon atom is represented with an asterisk as follows:

The priority order of the groups is: The bromine atom receives first priority, the (-CH2CH3) group second priority, the methyl group third and the hydrogen fourth.

The rotation is in clockwise direction, so the configuration would be R, but the least priority group is in the plane. Thus, the configuration would be reversed.

Therefore, the configuration of this compound is represented as follows:

(c)

The asymmetric carbon atom is represented with an asterisk as follows:

The priority order of the groups is: The alkene (CH=CH2) receive first priority, the (CH (CH3)2) group second priority, the methyl group third and the hydrogen fourth.

The rotation is in clockwise direction with the least priority group in below the plane. Thus, the configuration would be R.

Therefore, the configuration of this compound is represented as follows:

(d)

The asymmetric carbon atoms are represented with an asterisk as follows:

The groups are assigned as per priority order to the first asymmetric carbon as follows:

The...

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Chapter 5, Problem 6P is Solved
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Textbook: Organic Chemistry
Edition: 8
Author: L. G. Wade Jr
ISBN: 9780321768414

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Star (*) each asymmetric carbon atom in the following

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