Organic Chemistry : Stereochemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #31 : Stereochemistry

Which of the following best describes an S-enantiomer?

Possible Answers:

Levorotatory

Rotates light clockwise

Dextrorotatory

None of these

Correct answer:

None of these

Explanation:

S configuration deals with the arrangement of atoms around a chiral center. Levorotatory and dextrorotatory refer to the rotation of light (either clockwise or counter clockwise), which can only be calculated experimentally using a polarimeter to create plane polarized light. "Rotates light clockwise" is simply another way to say dextrorotatory. Therefore, none of the answer choices are correct.

Example Question #4 : Isomers

Stereoisomers

How many stereoisomers exist for the given compound?

Possible Answers:

Correct answer:

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 .

Example Question #5 : Help With Enantiomers

Chrial

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

Possible Answers:

Correct answer:

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, 

Example Question #6 : Help With Enantiomers

How many chiral centers does the given molecule have?

Possible Answers:

Correct answer:

Explanation:

There are 8 chiral centers which are marked below:

 

Prob 2

Carbon atoms need to be attached to 4 different groups to have a chiral center. Keep in mind that carbon atoms with a double bond can never be chiral. Looking at chiral center 1, the carbon is bonded to an alcohol group, a hydrogen atom, and two hydrocarbon groups. The hydrocarbon group clockwise is not identical to the hydrocarbon group counterclockwise. So this carbon would be considered bonded to 4 different groups making it chiral.

Example Question #7 : Help With Enantiomers

Prob 3

In the given molecule, what are the orientations of the top and bottom carbons respectively?

Possible Answers:

S,R

S,S

R,S

R,R

Correct answer:

R,R

Explanation:

The orientation of the chiral center is based on what the carbon is bonded to. The heaviest atom that the carbon is bonded is given higher priority. 

Top:Top   Bottom:Bottom

For the top carbon the oxygen is the heaviest, so it receives a 1, with the hydrogen as the least important group 4. The least priority group should be placed in the back, such as shown in the bottom example, before determining clockwise or counterclockwise orientation. For the bottom section, going from most important to least important groups, while ignoring the least important group, you get clock wise or  R orientation. 

Interpreting the top carbon is different because the least important group is not in the back. Reading from high to low priority, while the hydrogen is in the front, gives a S configuration (ignore the 4th priority group when rotating). Since the hydrogen group is opposite from where it should be, the orientation is opposite as well.

Example Question #3 : Help With Enantiomers

Prob 6

What is the orientation of the given molecule? 

Possible Answers:

R

Cis

Trans

S

Correct answer:

S

Explanation:

Label the priority of bonded groups first. 

Solution 6

Moving from first to second to third, which ignoring the 4th important group, gives a counterclockwise direction, or S.

Example Question #31 : Stereochemistry

Isomers that are nonsuperimposeable mirror images of each other are called __________.

Possible Answers:

enantiomers

conformers

constitutional isomers

diastereomers

Correct answer:

enantiomers

Explanation:

Enantiomers are chiral isomers of the same molecule that are mirror images of one another. Because of this characteristic, enantiomers cannot be placed on top of one another (superimposed) and yield the same molecule.

Example Question #11 : Help With Enantiomers

Cholic acid

How many stereocenters does the molecular framework of cholic acid (shown) have?

Possible Answers:

Correct answer:

Explanation:

Cholic acid 3d

There are 11 stereocenters, because here there are 11 asymmetric carbons and no E/Z isomerisms, nor planes of symmetry.

Example Question #32 : Stereochemistry

Cholic acid

How many possible stereoisomers does the molecular framework of cholic acid (shown) have?

Possible Answers:

Correct answer:

Explanation:

Cholic acid 3d

There are 11 stereocenters, because here there are 11 asymmetric carbons and no E/Z isomerisms, nor planes of symmetry. For compounds with no meso isomers or E/Z isomerisms, the possible number of stereoisomers is  where  is the number of stereocenters.

Example Question #12 : Help With Enantiomers

Cholic acid derivative

How many stereocenters does this steroid derivative have?

Possible Answers:

Correct answer:

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

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