Question 1

How many chiral centers are present in the Taxol molecule shown in the image?

Accepted Answer

11

Question 2

Given Taxol has 11 chiral centers, how many possible stereoisomers could exist for Taxol?

Accepted Answer

$$2^{11} = 2048$

Question 3

How many $$\pi$$ bonds are present in the Taxol molecule?

Accepted Answer

16

Question 4

What is the configuration (E or Z) around the double bond in Taxol?

Accepted Answer

E

Question 5

What is the correct IUPAC name for the compound shown in $$image_1 ($$first image)?

Accepted Answer

(2R,3S)-2,3-dichlorobutane

Question 6

What is the correct IUPAC name for the compound shown in $$image_2 ($$second image)?

Accepted Answer

(2S,4R,6R)-4-chloro-6-methyl-2-octanol

Question 7

What is the correct IUPAC name for the compound shown in $$image_3 ($$third image)?

Accepted Answer

(3S,4S)-4-chloro-3-hexanol

Question 8

A mixture of the R and S enantiomers of a compound has an observed rotation of $$-54. If $$the S enantiomer has a specific rotation of $$+60$$, what is the specific rotation of the R enantiomer?

Accepted Answer

$$-60$$

Question 9

A mixture of the R and S enantiomers of a compound has an observed rotation of $$-54. If $$the S enantiomer has a specific rotation of $$+60$$, what is the enantiomeric excess (ee) of this mixture?

Accepted Answer

90%

Question 10

A mixture of the R and S enantiomers of a compound has an observed rotation of $$-54. If $$the S enantiomer has a specific rotation of $$+60$$, what percentage of the mixture is the S enantiomer?

Accepted Answer

5%

Question 11

What is the relationship between the compounds shown in $$image_8$$ and $$image_9$$?

Accepted Answer

Diastereomers

Question 12

What is the relationship between the compounds shown in $$image_9$$ and $$image_10$$?

Accepted Answer

Diastereomers

Question 13

What is the relationship between the compounds shown in $$image_10$$ and $$image_11$$?

Accepted Answer

Enantiomers

Question 14

Which of the following best describes the mechanism of action of Taxol in cancer treatment?

Accepted Answer

Taxol arrests cells in mitosis, allowing apoptosis to occur.

Question 15

If a compound has two chiral centers, how many possible stereoisomers can it have?

Accepted Answer

$$2^2 = 4$

Question 16

Which of the following statements about enantiomers is correct?

Accepted Answer

Enantiomers have identical physical properties except for their interaction with plane-polarized light.

Question 17

Which compound would be optically inactive?

Accepted Answer

A racemic mixture of enantiomers

Question 18

If a compound has a dashed wedge for bromine and a solid wedge for chlorine, what is the relationship between this compound and its mirror image?

Accepted Answer

They are enantiomers.

Question 19

Which of the following best describes the stereochemistry of (2R,3S)-2,3-dichlorobutane?

Accepted Answer

The chlorine at C-2 is on a wedge and the chlorine at C-3 is on a dash.

CHP 4 STUDY GUIDE

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