Q: Which of the following is the most important resonance contributor for the acetate ion ($\mathrm{CH_3COO^-}$)?

Both oxygen atoms share the negative charge equally

Q: Which of the following statements about the SN2 reaction mechanism is correct?

The reaction rate depends on the concentration of both nucleophile and substrate

Q: Which of the following is the slowest step in a multi-step reaction mechanism?

The step with the highest activation energy ($E_a$)

Q: Which of the following transformations is an example of a retro-synthetic step? A. Breaking a C–C bond to reveal simpler precursors B. Forming a new C–C bond C. Oxidizing an alcohol to a ketone D. Reducing a ketone to an alcohol

A. Breaking a C–C bond to reveal simpler precursors

Q: Which of the following best explains the observed stereochemical outcome in the anti addition of Br$_2$ to cyclohexene?

Formation of a bromonium ion intermediate followed by backside attack

Q: Which of the following is the correct assignment of configuration for the chiral center in (R)-2-butanol?

OH group is assigned highest priority, followed by ethyl, methyl, and hydrogen

Question 1

Which of the following molecules is the most acidic?

$\mathrm{CH_3CH_2OH}$, $\mathrm{CH_3COOH}$, $\mathrm{CH_3CH_2NH_2}$, $\mathrm{CH_3CH_3}$

Accepted Answer

$\mathrm{CH_3COOH}$

Question 2

Which of the following compounds has the highest number of stereogenic centers?

A. $\mathrm{2,3-dibromobutane}$
B. $\mathrm{2-bromobutane}$
C. $\mathrm{1,2-dibromoethane}$
D. $\mathrm{2-chloropropane}$

Accepted Answer

A. $\mathrm{2,3-dibromobutane}$

Question 3

Which conformation of butane is the most stable?

A. Fully eclipsed
B. Gauche
C. Anti
D. Partially eclipsed

Accepted Answer

C. Anti

Question 4

Rank the following in order of increasing oxidation state of the indicated carbon atom:

A. $\mathrm{CH_3CH_2OH}$
B. $\mathrm{CH_3CHO}$
C. $\mathrm{CH_3COOH}$
D. $\mathrm{CH_3CH_3}$

Accepted Answer

D < A < B < C

Question 5

Which of the following is the correct IUPAC name for the structure below?

A molecule with a five-carbon chain, a bromo substituent on carbon 4, and an ethyl group on carbon 3.

Accepted Answer

4-bromo-3-ethylpentane

Question 6

Which reagent would you use to convert cyclohexene to trans-1,2-cyclohexanediol?

Accepted Answer

mCPBA followed by aqueous acid

Question 7

What is the major product when 2-methyl-2-butene reacts with Br$_2$ in CCl$_4$?

Accepted Answer

2,3-dibromo-2-methylbutane

Question 8

Which of the following best describes the mechanism for the reaction of 1-bromopropane with NaOH to form 1-propanol?

Accepted Answer

SN2 substitution

Question 9

Which of the following is the most important resonance contributor for the acetate ion ($\mathrm{CH_3COO^-}$)?

Accepted Answer

Both oxygen atoms share the negative charge equally

Question 10

In the $^1$H NMR spectrum, which chemical shift is most likely to correspond to an aromatic proton?

Accepted Answer

7.5 ppm

Question 11

Which IR absorption is characteristic of a carbonyl group ($\mathrm{C=O}$)?

Accepted Answer

Around 1700 cm$^{-1}$

Question 12

Which of the following reagents would convert a ketone to a secondary alcohol?

Accepted Answer

NaBH$_4$

Question 13

Which of the following statements about the SN2 reaction mechanism is correct?

Accepted Answer

The reaction rate depends on the concentration of both nucleophile and substrate

Question 14

Which of the following is the slowest step in a multi-step reaction mechanism?

Accepted Answer

The step with the highest activation energy ($E_a$)

Question 15

Which of the following transformations is an example of a retro-synthetic step?

A. Breaking a C–C bond to reveal simpler precursors
B. Forming a new C–C bond
C. Oxidizing an alcohol to a ketone
D. Reducing a ketone to an alcohol

Accepted Answer

A. Breaking a C–C bond to reveal simpler precursors

Question 16

Which of the following best explains the observed stereochemical outcome in the anti addition of Br$_2$ to cyclohexene?

Accepted Answer

Formation of a bromonium ion intermediate followed by backside attack

Question 17

Which of the following is the correct assignment of configuration for the chiral center in (R)-2-butanol?

Accepted Answer

OH group is assigned highest priority, followed by ethyl, methyl, and hydrogen

Question 18

Which of the following is a diastereomer of (2R,3R)-2,3-dibromobutane?

Accepted Answer

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

Question 19

Which of the following is the major product when cyclohexanone is treated with NaBH$_4$ in methanol?

Accepted Answer

Cyclohexanol

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