Organic Chemistry : Isomers

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #81 : Stereochemistry

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Which of these molecules is a meso compound?

Possible Answers:

II and III

IV only

III only

I only

II only

Correct answer:

III only

Explanation:

A molecule is meso if it contains at least two stereocenters, but is rendered optically inactive by internal structural symmetry. In other words, a meso compound may be split in half in some way such that portions on either side of an imaginary line are mirror images. Note: The absolute configurations of a meso compound with two stereocenters are opposite (R/S). The internal symmetry that makes molecule III a meso compound is best conveyed through a Haworth projection:

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Example Question #61 : Isomers

How many possible stereoisomers does the product of the following reaction have?

Cl cl meso compound

Possible Answers:

Correct answer:

Explanation:

Cl cl meso answer

This is the product of the given reaction. Remember, anti elimination is favored over the Zaitsev product. All possible stereoisomers with methyl groups syn are meso compounds. Of the possible stereoisomers with methyl groups anti, there are two pairs of identical structures. Thus there are only 2 possible stereoisomers.

Example Question #1 : Help With Meso Compounds

S or r

How many of the existing configurational stereoisomers are chiral? 

Possible Answers:

2

3

1

None

Correct answer:

2

Explanation:

There are three configurational stereoisomers. These include the RS, SS, and RR isomers. Since one of them, the RS isomer, has a plane of symmetry, it is achiral, and the other two are chiral.

Example Question #6 : Help With Meso Compounds

S or r

How many configurational stereoisomers exist for this structure? 

Possible Answers:

3

1

2

4

Correct answer:

3

Explanation:

There are two tetrahedral asymmetrical stereocenters in this molecule (the carbon atoms attached to each of the chlorine atoms). Thus, the combinations of R and S include RR, RS, SR, and SS. Note the plane of symmetry in the molecule; RS and SR are the same molecule (meso compounds). Thus, there are three distinct configurational stereoisomers of this compound. 

Example Question #1 : Epimers

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The given molecules are __________.

Possible Answers:

constitutional isomers

stereoisomers

conformers

None of these

identical

Correct answer:

stereoisomers

Explanation:

Stereoisomers have different orientations around a single stereocenter. The two molecules are stereoisomers. Specifically, these molecules are epimers, meaning that they differ at only one stereocenter.

Constitutional isomers have the same molecular formula, but different structures. Conformers have different rotations around a single bond. The molecules are clearly not identical.

Example Question #2 : Epimers

Which of the following carbons represents the stereogenic center between the given isomers?

Linear glucoseLinear galactose

Possible Answers:

Carbon 2

Carbon 4

Carbon 1

Carbon 5

Carbon 3

Correct answer:

Carbon 4

Explanation:

Epimers are isomers that have different configurations at only one carbon atom. This carbon atom is known as the stereogenic center. The given compounds are identical except for the orientation around carbon number 4; thus, carbon 4 is the stereogenic center.

Example Question #81 : Stereochemistry

Which of these describes an epimer?

Possible Answers:

One of a pair of stereoisomers, which differ in configuration at only one stereogenic center

Stereoisomers that are not superimposable mirror images

Two or more stereoisomers of a compound which have different configurations at one or more (but not all) of the equivalent stereocenters and are not mirror images of each other

There are no such things as epimers.

Correct answer:

One of a pair of stereoisomers, which differ in configuration at only one stereogenic center

Explanation:

In organic chemistry, an epimer refers to one of a pair of stereoisomers, which differ in configuration at only one stereogenic center. Any other stereogenic centers in the compounds are the same in each one. The sugars glucose and galactose are epimers.

Diastereomerism occurs when two or more stereoisomers of a compound have different configurations at one or more, but not all, of the equivalent stereocenters. These stereoisomers are not mirror images of each other. D-erythrose and D-threose are diastereomers.

Note: Epimers are diastereomers that contain more than one stereocenter but differ from each other in the configuration at ONLY one stereocenter. Diastereomers can differ at more than one stereocenter, but not all of them.

Enantiomers are stereoisomers that are non-superimposable mirror images. This means that the molecules cannot be placed on top of one another and give the same molecule. D-threose and L-threose are enantiomers.

Example Question #1 : Stereochemistry

The molecules shown below are best described as __________.

Molecules

Possible Answers:

diastereomers

isomers

epimers

enantiomers

Correct answer:

isomers

Explanation:

The molecules in this problem are isomers because they each have unique configurations and do not share the same funcitonal groups at the same carbon positions. Enantiomers are reflections of each other. Diastereomers are stereoisomers that differ at one or more stereocenters, while epimers are stereoisomers that differ at only one stereocenter.

Example Question #1 : Help With Comformers

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In the most stable chair conformation of the following Haworth projection, the bromine at carbon 1, the hydroxide at carbon 2, and the hydroxide at carbon 4 are __________, __________, and __________, respectively.

 

Possible Answers:

equatorial up . . . axial down . . . equatorial up

equatorial up . . . equatorial down . . . axial up

axial up . . . equatorial down . . . equatorial up

equatorial down . . . equatorial up . . . axial down

axial down . . . equatorial up . . . equatorial down

Correct answer:

equatorial up . . . equatorial down . . . axial up

Explanation:

Based on the Haworth projection given, the relative orientations of the three substituents are bromine up, hydroxide: down, hydroxide: up. In the most stable chair conformation, the largest substituents are oriented equatorial. If bromine is oriented equatorial up, the hydroxide at carbon 2 is equatorial down and the hydroxide at carbon 4 is axial up.

Example Question #2 : Help With Comformers

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What is the relationship between these compounds?

Possible Answers:

Diastereomers

Constitutional isomers

Enantiomers

Meso

Conformational isomers

Correct answer:

Conformational isomers

Explanation:

The two given molecules are conformational isomers. The molecules are superimposable by horizontally rotating either structure 180 degrees and rotating the bond between carbons 2 and 3. Both enantiomers and diastereomers are non-superimposable and constitutional isomers must have non-configurational differences in structure. There is no internal plane of symmetry, thus neither compound can be meso.

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