Organic Chemistry : Help with Enantiomers

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

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Example Question #65 : Stereochemistry

What is the absolute configuration of the molecule shown?

Img 1240

Possible Answers:

2S, 4S

2R, 4S

2R, 4R

2S, 4R

Correct answer:

2R, 4S

Explanation:

This molecule has two stereocenters. Numbering from left to right they are carbon numbers  and .

For the chiral carbon on the left (carbon number ) The bromine group is first priority, the rest of the molecule on the right is second priority, the methyl group on the left is third priority, and the hydrogen (not drawn) is the fourth (lowest) priority. Placing the fourth priority away from the viewer, into the plane of the page/screen (on a dash), the order of the substituents from highest to lowest priority is , which follows a clockwise directionality, so the absolute configuration is R.

For the chiral carbon on the left (carbon number ) The bromine group is first priority, the rest of the molecule on the left is second priority, the methyl group on the right is third priority, and the hydrogen (not drawn) is the fourth (lowest) priority. Placing the fourth priority away from the viewer, into the plane of the page/screen (on a dash), the order of the substituents from highest to lowest priority is , which follows a counterclockwise directionality, so the absolute configuration is S.

Example Question #41 : Isomers

S or r

Assign absolute configuration to the tetrahedral asymmetric stereocenter (TAS) circled in red.

Possible Answers:

Trans

S

Cis

R

Correct answer:

S

Explanation:

Aside from the hydrogen that extends "back into the page", priority 1 goes to the top right group (from the perspective of the TAS) because of the large chlorine atom. Priority 2 goes to the top left group because of the carbon atom attached to another carbon atom. Priority 3 goes to the methyl group because it is a carbon atom attached to hydrogen atoms, which have the lowest priority. When the hydrogen atom attached to the TAS is viewed as going back into the page, the circle created by going from priority 1 to priority 3 is counterclockwise, so we assign this TAS to be S. Cis and trans are irrelevant to TAS. 

Example Question #42 : Isomers

S or r

Assign absolute configuration to the tetrahedral asymmetric center (TAS) circled in blue. 

Possible Answers:

R

Cis

Trans

S

Correct answer:

R

Explanation:

Aside from the hydrogen that extends "forward from the page", priority 1 goes to the top left group (from the perspective of the TAS) because of the chlorine atom. Priority 2 goes to the bottom left group because of the carbon atom attached to another two carbon atoms. Priority 3 goes to the bottom right group, which has a carbon attached to only one other carbon at the point of difference with the group that has priority 2. When the hydrogen atom attached to the TAS is viewed as going back into the page, the circle created by going from priority 1 to priority 3 is clockwise, so we assign this TAS to be R. Cis and trans are irrelevant to TAS. 

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