Question 1

Which of the following best describes the mechanism for the reaction of an alkene with $$\mathrm{Br_2$}$$ under UV light?

Accepted Answer

A free radical mechanism involving homolytic cleavage of $$\mathrm{Br_2$}$$

Question 2

What is the correct IUPAC name for a compound with the following structure: a six-carbon chain with a bromo substituent on carbon 2 and a methyl group on carbon 4?

Accepted Answer

4-Methyl-2-bromohexane

Question 3

Given the reaction: $$\mathrm{CH_3CH_2Br}$$ + $$\mathrm{NaCN}$$ $$\rightarrow$$ $$\mathrm{CH_3CH_2CN}$$ + $$\mathrm{NaBr}$$, what type of reaction mechanism is most likely?

Accepted Answer

An $$\mathrm{S_N2}$$ mechanism

Question 4

Which of the following acid-base reactions favors the formation of products at equilibrium? $$\mathrm{CH_3CO_2H}$$ + $$\mathrm{OH^-}$$ $$\rightarrow$$ $$\mathrm{CH_3CO_2^-}$$ + $$\mathrm{H_2O}$$

Accepted Answer

The reaction favors products because water is a weaker acid than acetic acid.

Question 5

Assign the R/S configuration to the following chiral center: $$\mathrm{CH_3CH(OH)CH_2Br} at $$the carbon bearing the OH group.

Accepted Answer

R

Question 6

Which of the following pairs are enantiomers?

Accepted Answer

Two molecules that are non-superimposable mirror images

Question 7

Which of the following best describes the relationship between (R)-2-butanol and (S)-2-butanol?

Accepted Answer

They are enantiomers.

Question 8

In the reaction of $$\mathrm{CH_3CH_2OH}$$ with $$\mathrm{HBr}$$, what is the major organic product?

Accepted Answer

$$\mathrm{CH_3CH_2Br}$$

Question 9

Which of the following statements about Fischer projections is correct?

Accepted Answer

Horizontal lines represent bonds coming out of the plane toward the viewer.

Question 10

Which of the following best explains why $$\mathrm{Br_2$}$$ reacts with alkenes but not with alkanes under normal conditions?

Accepted Answer

Alkenes have a high electron density in the $$\pi$$ bond, making them more reactive toward electrophiles.

Question 11

Which of the following is the correct order of acid strength (from strongest to weakest) for the following acids: $$\mathrm{H_2O}$$, $$\mathrm{CH_3CO_2H}$$, $$\mathrm{NH_3$}$$?

Accepted Answer

$$\mathrm{CH_3CO_2H} \u003e \mathrm{H_2O} \u003e \mathrm{NH_3$}$$

Question 12

Which of the following best describes the stereochemical outcome when a chiral alkyl bromide undergoes an $$\mathrm{S_N2}$$ reaction?

Accepted Answer

Inversion of configuration at the chiral center

Question 13

Which of the following is a correct statement about diastereomers?

Accepted Answer

Diastereomers are stereoisomers that are not mirror images.

Question 14

Which of the following best explains why $$\mathrm{NaCN} is a $$good nucleophile in $$\mathrm{S_N2}$$ reactions?

Accepted Answer

The cyanide ion is small and has a high electron density on the carbon atom.

Organic Chemistry Study Guidance: Acid-Base Equilibria, Stereochemistry, and Fischer Projections

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