Q: Which of the following Fischer projections represents the enantiomer of the following compound? $$\begin{array}{c} \text{CHO} \\ \text{OH} \\ \text{H} \\ \text{CH}_2\text{OH} \end{array}$$

$$\begin{array}{c} \text{CHO} \\ \text{H} \\ \text{OH} \\ \text{CH}_2\text{OH} \end{array}$$

Q: Which of the following reactions will result in a racemic mixture?

Reaction of a chiral alkyl halide with $$\text{H}_2\text{O}$$ via an $$S_N1$$ mechanism

Question 1

Which of the following statements best describes enantiomers?

Accepted Answer

They are stereoisomers that are non-superimposable mirror images of each other.

Question 2

Given the Fischer projections below, which pair represents diastereomers?

$$\begin{array}{c}
	ext{CHO} \
	ext{H} \
	ext{OH} \
	ext{CH}_2	ext{OH}
\end{array}$$

and

$$\begin{array}{c}
	ext{CHO} \
	ext{OH} \
	ext{H} \
	ext{CH}_2	ext{OH}
\end{array}$$

Accepted Answer

They are enantiomers.

Question 3

Assign the absolute configuration (R or S) to the chiral center in the following molecule:

$$\begin{array}{c}
	ext{CHO} \
	ext{H} \
	ext{OH} \
	ext{CH}_2	ext{OH}
\end{array}$$

Accepted Answer

$$S$$

Question 4

Which of the following is true about diastereomers?

Accepted Answer

They have different physical and chemical properties.

Question 5

Which of the following Fischer projections represents the enantiomer of the following compound?

$$\begin{array}{c}
	ext{CHO} \
	ext{OH} \
	ext{H} \
	ext{CH}_2	ext{OH}
\end{array}$$

Accepted Answer

$$\begin{array}{c}
	ext{CHO} \
	ext{H} \
	ext{OH} \
	ext{CH}_2	ext{OH}
\end{array}$$

Question 6

Which of the following is the most stable carbocation?

Accepted Answer

Tertiary carbocation

Question 7

Which of the following is the best leaving group in an SN1 reaction?

Accepted Answer

$$	ext{I}^-$$

Question 8

Which of the following reactions will result in a racemic mixture?

Accepted Answer

Reaction of a chiral alkyl halide with $$	ext{H}_2	ext{O}$$ via an $$S_N1$$ mechanism

Question 9

Which of the following is the correct product for the reaction of cyclohexene with $$	ext{Br}_2 in$$ $$	ext{CCl}_4$$?

Accepted Answer

Trans-1,2-dibromocyclohexane

Question 10

Which of the following statements about the E2 elimination mechanism is correct?

Accepted Answer

It requires a strong base and anti-coplanar geometry.

Question 11

Which of the following is the major product when 2-bromobutane reacts with $$	ext{NaOEt} in $$ethanol?

Accepted Answer

Trans-2-butene

Question 12

Which of the following best describes the stereochemistry of the product formed when cyclohexene reacts with $$	ext{Br}_2 in$$ $$	ext{CCl}_4$$?

Accepted Answer

Anti addition, resulting in trans-1,2-dibromocyclohexane

Question 13

Which of the following is the correct order of stability for the following carbocations: methyl, primary, secondary, tertiary?

Accepted Answer

Tertiary \u003e Secondary \u003e Primary \u003e Methyl

Question 14

Which of the following is the best nucleophile in a polar aprotic solvent?

Accepted Answer

$$	ext{I}^-$$

Question 15

Which of the following is the correct product for the reaction of 1-butyne with $$	ext{NaNH}_2$$ followed by $$	ext{CH}_3	ext{Br}$$?

Accepted Answer

2-pentyne

Question 16

Which of the following is the correct product for the reaction of cyclohexanone with $$	ext{NaBH}_4$$?

Accepted Answer

Cyclohexanol

Question 17

Which of the following is the correct product for the reaction of 2-methyl-2-butene with $$	ext{HBr}$$?

Accepted Answer

2-bromo-2-methylbutane

Question 18

Which of the following is the correct product for the reaction of 1,3-butadiene with $$	ext{Br}_2 at $$low temperature?

Accepted Answer

1,2-dibromo-3-butene

Question 19

Which of the following is the correct product for the reaction of benzene with $$	ext{Br}_2$$ and $$	ext{FeBr}_3$$?

Accepted Answer

Bromobenzene

Organic Chemistry Stereochemistry and Reaction Mechanisms Study Guide

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