Help with Enantiomers

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Organic Chemistry › Help with Enantiomers

Questions 1 - 10
1

What are the absolute configurations at carbons labelled , , and in the molecule below, respectively?

Screen shot 2015 11 09 at 6.00.01 pm

S, R, R

R, S, R

S, S, R

S, R, S

Explanation

Carbon number : Hydroxyl is , group going up is , group going down is . Therefore it's S. Carbon number : Group going to chloride is , group going to hydroxyl is , methyl is . Therefore it's R. Carbon number : Chloride is , group going up is , group going down is . Therefore it's R.

2

What is the IUPAC name for the given organic molecule?

Screen shot 2015 09 21 at 1.19.58 pm

(2R, 4S)-4,5,5-trimethylhexan-2-ol

(2R, 4R)-4,5,5-trimethylhexan-2-ol

(2S, 4R)-4,5,5-trimethylhexan-2-ol

(3S, 5R)-2,2,3-trimethylhexan-5-ol

(3R, 5R)-2,2,3-trimethylhexan-5-ol

Explanation

The absolute configuration around carbons 2 and 4 is R and S, respectively. The molecule is a hexanol, and the numbering starts with the carbon closest to the hydroxyl group.

3

How many stereoisomers would be obtained by the hydrogenation of compound C?

Mcat_1

Two

One

Three

Four

Zero

Explanation

The hydrogenation of compound Cwould add two hydrogen atoms across the double bond, but would generate only one new stereocenter. This stereocenter would be found on the third carbon in the chain (from the right), which would be bound to the phenyl substituent, a methyl group, a hydrogen atom, and the remaining branched carbon chain.

The hydrogenation reaction would create a racemic mixture of both possible orientations of this stereocenter, with both enantiomers present in equal amounts. There would this be two stereoisomer products obtained from the hydrogenation of compound C.

4

Cholic acid derivative

How many stereocenters does this steroid derivative have?

Explanation

There are 11 asymmetric carbons and one E double bond, so there are 13 stereocenters in total. For each E/Z isomerism, there are 2 stereocenters.

Cholic acid derivative 3d

5

How many stereoisomers are possible for the compound 2,3,4-trimethylpentane?

One

Two

Three

Four

Five

Explanation

2,3,4-trimethylpentane does not contain any stereocenters. The structure is a five-carbon chain, with the end carbons bonded to three hydrogens each. The three central carbons each carry a methyl group and a hydrogen atom.

Remember that a stereocenter is only present when a carbon is bound to four different substituents. The 2 and 4 carbons both have two methyl groups (the end carbons and the added groups), so they would contain a plane of symmetry and would not be stereocenters. Likewise, a plane of symmetry exists at the 3 carbon; the substituents toward the 1 carbon and 5 carbon are the same. This compound, therefore, would have no stereocenters and could only exist as one stereoisomer.

6

Stereoisomers

How many stereoisomers exist for the given compound?

Explanation

In this question, we're presented with the structure of a compound and we're asked to determine how many stereoisomers for this compound exists. It's important to remember that stereoisomers are compounds that have the same chemical formula and the same connectivity between its atoms, but what sets them apart is how their atoms are oriented in space.

When looking at the structure of the molecule in the question, we can see that there are two chiral carbons (carbons with four different substituents bound). A chiral carbon can have its substituents bound in two different ways, either R or S. Since each chiral carbon has two possible configurations of its atoms, the total numbers of possible stereoisomers is equal to , where is equal to the number of chiral carbons. Thus, we can conclude that the number of stereoisomers is equal to .

7

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

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

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

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

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

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

8

Chrial

How many different stereoisomer orientations are possible for the given molecule?

Explanation

There are 5 different chiral centers in the molecule as shown below:

Solution

In order for a carbon to be a chiral center, it must be bonded to 4 different groups. The total number of possible stereoisomers is equal to , where n is the number of chiral centers. So in this case,

9

What is the IUPAC name for the molecule shown?

Screen shot 2015 11 12 at 6.01.33 pm

(2R,3S)-3-methyl-2-pentanol

(2R,3R)-3-methyl-2-pentanol

(2S,3S)-3-methyl-2-pentanol

(2S,3R)-3-methyl-2-pentanol

Explanation

Carbon number : hydroxyl is first priority, The rest of the molecule is second, methyl is third. Placing in back makes go clockwise. Therefore, it is R. Carbon number : alkyl with hydroxyl is first priority, The rest of the molecule is second, methyl is third. Placing in back makes go counterclockwise. Therefore, it is S.

10

What is the absolute configuration of the compound shown?

Img 1226

R

S

This molecule is achiral.

1R, 2S

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.

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