Organic Chemistry : Isomers

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #63 : Stereochemistry

What is the absolute configuration of the molecule shown?

Img 1228

Possible Answers:

1R, 3S

1R, 3R

1S, 3S

1S, 3R

Correct answer:

1S, 3S

Explanation:

This molecule contains two stereocenters, at carbon number  (containing the hydroxyl group), and carbon number  (containing the methyl group). 

For carbon , the hydroxyl group is first priority, the alkane group going across the top of the molecule is second priority, the alkane group going down the left side of the molecule 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.

For carbon  , the alkane group moving across the top of the molecule toward the hydroxyl group is first priority, the alkane group going down the right side of the molecule is second priority, the methyl group 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 #36 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1230

Possible Answers:

R

S

This molecule is achiral

2E, 3S

Correct answer:

S

Explanation:

In the molecule shown, carbon number  (numbering with the alkene terminal carbon as number ), is the only stereocenter. The alkene group is first priority, the ethyl group is second priority, the methyl group 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 #37 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1231

Possible Answers:

This molecule is achiral.

S

1R, 2S

R

Correct answer:

R

Explanation:

In the molecule shown, carbon  is the only stereocenter. The fluorine group is first priority, the alkyl branch containing the amino group is second priority, the methyl group 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.

Example Question #31 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1233

Possible Answers:

2S, 3R

2R, 3R

2R, 3S

1S, 2S

Correct answer:

2R, 3S

Explanation:

For the top chiral carbon (carbon number ), The hydroxyl group is first priority, the cyanide group is second priority, the branch forming the rest of the backbone is third priority, and the hydrogen 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 bottom chiral carbon (carbon number ), the hydroxyl group is first priority, the branch forming the top of the backbone is second priority, the  group is third priority, and the hydrogen 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 #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. 

Example Question #44 : Isomers

https://vt-vtwa-assets.varsitytutors.com/vt-vtwa/uploads/problem_question_image/image/2655/MCAT_7.jpg

How are the given molecules related?

Possible Answers:

Structural isomers

Enantiomers

They have different molecular formulas

Identical

Diastereomers

Correct answer:

Identical

Explanation:

The given images are Fisher projections of the molecules. To compare them, we must mentally rotate the substituents around the carbon-carbon bond through the molecule's center, as well as consider flipping the projection end-over-end.

If the molecule to the left were flipped directly end-over-end, it will match the molecule to the right, with the methyl pointed upward in the front plane and the ethyl pointed downward in the rear plane. These molecules are identical.

Example Question #1 : Help With Diastereomers

Img 20150723 132858

Label each stereocenter in the molecule above as R or S.

Possible Answers:

2S, 3S

1R, 3S

1S, 2S, 3S

2R, 3R

Correct answer:

2S, 3S

Explanation:

Carbon 1 is not a stereocenter as both constituents on the carbon are identical. For carbon 2, the bromine is the attachment with the most priority, followed by carbon 3, then carbon 1. Because bromine is in the back, the stereocenter is designated as an S. For carbon 3, the alcohol group is the attachment with the most priority, followed by carbon 2, then carbon 4. Because alcohol is in the front, the stereocenter is designated as an S.

Example Question #2 : Help With Diastereomers

What is the stereochemical relationship between these molecules?

4

Possible Answers:

Conformational isomers

Identical compounds

Enantiomers

Diastereomers

Correct answer:

Diastereomers

Explanation:

The molecules shown contain three stereocenters as evidenced by the bonds of carbons 2, 3, and 4 to four unique groups. Rotating the molecule on the right 180 degrees in the horizontal plane reveals that only carbon 2 differs in absolute configuration (R/S). As a general rule, switching the absolute configurations of all stereocenters present in a compound yields its enantiomer. Switching the configuration at least one stereocenter, but not all, yields diastereomers, non-superimposable stereoisomers that are not mirror images. The two molecules shown are diastereomers. A molecular modeling kit can prove extremely useful in visualizing the difference in such situations.

 

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