Organic Chemistry : Stereochemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #51 : Stereochemistry

What is the IUPAC name for the molecule shown below?

Screen shot 2015 11 09 at 6.07.55 pm

Possible Answers:

(4E,3S)-3,5-dimethyl-4-pentene

(4Z,3R)-3,5-dimethyl-4-pentene

(3E,5R)-3,5-dimethyl-3-pentene

(3E,5S)-3,5-dimethyl-3-pentene

Correct answer:

(3E,5S)-3,5-dimethyl-3-pentene

Explanation:

Numbering goes from right to left, so double bond is attributed to carbon #. The double bond is E, because higher priority groups are across the double bond from each other. Carbon # is S.

Example Question #22 : Help With Enantiomers

Which of the following statements best describes enantiomers?

Possible Answers:

Enantiomers are stereoisomers that are achiral.

None of these are true.

Enantiomers are stereoisomers that have symmetry along a mirror plane.

Enantiomers are stereoisomers that have non-identical mirror image conformations.

Enantiomers are stereoisomers that have identical mirror image conformations.

Correct answer:

Enantiomers are stereoisomers that have non-identical mirror image conformations.

Explanation:

Enantiomers are stereoisomers that have non-identical mirror image conformations and they are chiral as well. They are also non-superimposable which means, when placed on top of each other, they do not look the same.

Example Question #51 : Stereochemistry

If (+)-oxalic acid rotates light by  then by how much would (-)-oxalic acid rotate light?

Possible Answers:

Correct answer:

Explanation:

(+)-Oxalic acid is the enantiomer of (-)-oxalic acid and will therefore rotate light in the opposite direction, to the same magnitude. Since (+)-oxalic acid rotates light a positive 32 degrees, (-)-oxalic acid will rotate light by an equal magnitude, but opposite (negative) 32 degrees. The correct answer is: .

Example Question #31 : Isomers

What is the absolute configuration of the compound shown?

Img 1226

Possible Answers:

S

This molecule is achiral.

R

1R, 2S

Correct answer:

R

Explanation:

The only stereocenter in this molecule is at the topmost carbon. The hydroxyl group is first priority, the alkene is second priority, the alkane 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 #32 : Isomers

If (1S,3S)-1-chloro-3-methylcyclohexane undergoes a substitution reaction when reacted with , what product will predominate?

Possible Answers:

A 50/50 mixture of (1S,3S)-1,3-dimethylcyclohexane and (1S,3R)-1,3-dimethylcyclohexane

(1R,3S)-1,3-dimethylcyclohexane

(1R,3R)-1,3-dimethylcyclohexane

(1S,3S)-1,3-dimethylcyclohexane

(1S,3R)-1,3-dimethylcyclohexane

Correct answer:

(1S,3S)-1,3-dimethylcyclohexane

Explanation:

This reaction would proceed by an  mechanism, which will result in inversion of configuration at the carbon of interest. However, due to priority, the classification of the chiral center of interest does not change. Therefore, (1S,3S)-1,3-dimethylcyclohexane is the correct answer. Keep in mind, however, that elimination would be a major pathway under these conditions as well. 

Example Question #26 : Help With Enantiomers

Nicotine, whose structure is shown below, is one of the major compounds found in cigarettes. As it turns out, nicotine has different stereoisomers. Which of the carbon atoms found in nicotine's molecular structure allows it to have different stereoisomers?

Nicotine

Possible Answers:

Carbon 

Carbon 

Carbon 

Carbon 

Correct answer:

Carbon 

Explanation:

In this question, we're given the molecular structure of nicotine. We're also told that nicotine has various stereoisomers, and we're asked to identify which carbon atom would allow for nicotine to have different stereoisomers.

In order for a compound to have various stereoisomers of itself, it needs to contain at least one chiral carbon atom. A chiral carbon is one that is asymmetrical. In other words, this carbon atom is bonded to four different substituents. Therefore, when looking at the molecular structure of nicotine, we need to look for a carbon atom that has four different substituents.

As we can see in the structure shown, the only carbon atom that meets this requirement is carbon . While it isn't shown here explicitly, we know that there is also a lone hydrogen atom bonded to this carbon. Consequently, as a result of having only one chiral carbon atom, nicotine can exist in two stereoisomeric forms as enantiomers, shown below.

Nicotine enantiomer 1Nicotine enantiomer 2

Example Question #31 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1227

Possible Answers:

1Z, 2S

R

This molecule is achiral

S

Correct answer:

S

Explanation:

The only stereocenter in this molecule is carbon number . The chlorine group is first priority, the carboxyl goup is second priority, the alkane 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 #32 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1232

Possible Answers:

S

This molecule is achiral

R

2R, 3Z

Correct answer:

S

Explanation:

In the molecule shown, carbon  is the only stereocenter. The hydroxyl group is first priority, the alkyne 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 #33 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1234

Possible Answers:

R

S

This molecule is achiral

1S, 2R

Correct answer:

S

Explanation:

 In the molecule shown, carbon  is the only stereocenter. The amino group is first priority, the carboxyl group is second priority, the methyl 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 #34 : Help With Enantiomers

What is the absolute configuration of the molecule shown?

Img 1235

Possible Answers:

R, Z

S, E

S, Z

R, E

Correct answer:

R, E

Explanation:

In the molecule shown are two stereocenters, carbon  and the alkene bond (double bond). For carbon , the hydroxyl group is first priority, the alkene 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.

For the alkene bond, the higher priority substituents are on opposite sides of the double bond. The one-letter designation for this type of geometric arrangement of substituents across a double bond is E.

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