Question 1

Which of the following alcohols is the most acidic?

A) Cyclohexanol 
B) 1-Butanol 
C) 1,2-Ethanediol 
D) 1,2,3-Propanetriol

Accepted Answer

D) 1,2,3-Propanetriol

Question 2

Which compound reacts fastest with acidic water in an electrophilic aromatic substitution?

A) Benzene 
B) Toluene 
C) Nitrobenzene 
D) Biphenyl

Accepted Answer

B) Toluene

Question 3

Which of the following compounds is most soluble in water?

A) 2,2-Dimethylpropane 
B) 1-Butanol 
C) 1-Octanol 
D) 1-Hexanol

Accepted Answer

B) 1-Butanol

Question 4

Which reagent would best convert 5-methyl-1-hexene to 5-methyl-1-hexanol via anti-Markovnikov addition?

A) $\mathrm{H_2O, H_2SO_4}$ 
B) $\mathrm{BH_3 \cdot THF, H_2O_2, OH^-}$ 
C) $\mathrm{Br_2, H_2O}$ 
D) $\mathrm{Hg(OAc)_2, H_2O}$

Accepted Answer

B) $\mathrm{BH_3 \cdot THF, H_2O_2, OH^-}$

Question 5

Which alkene is most stable?

A) 2-Methyl-2-butene 
B) 1-Butene 
C) cis-2-Butene 
D) trans-2-Butene

Accepted Answer

A) 2-Methyl-2-butene

Question 6

What is the major product when cyclohexene is treated with $\mathrm{KMnO_4}$ and $\mathrm{H_2O}$?

A) Cyclohexanol 
B) Cyclohexanone 
C) cis-1,2-Cyclohexanediol 
D) trans-1,2-Cyclohexanediol

Accepted Answer

C) cis-1,2-Cyclohexanediol

Question 7

Which sequence of reagents would convert an alkyne to a cis-alkene?

A) $\mathrm{H_2, Pd/C}$ 
B) $\mathrm{H_2, Lindlar's~catalyst}$ 
C) $\mathrm{Na, NH_3}$ 
D) $\mathrm{Br_2, CH_2Cl_2}$

Accepted Answer

B) $\mathrm{H_2, Lindlar's~catalyst}$

Question 8

What is the IUPAC name for the following compound?

(CH$_3$)$_2$CHCH$_2$CH$_2$OH

Accepted Answer

C) 3-Methyl-1-pentanol

Question 9

Which of the following is the preferred product when 1-butanol is oxidized with $\mathrm{PCC}$?

A) Butanoic acid 
B) 1-Butanal 
C) 2-Butanone 
D) 1-Butene

Accepted Answer

B) 1-Butanal

Question 10

Which reagent would best reduce a carboxylic acid to a primary alcohol?

A) $\mathrm{NaBH_4}$ 
B) $\mathrm{LiAlH_4}$ 
C) $\mathrm{H_2, Pd/C}$ 
D) $\mathrm{KMnO_4}$

Accepted Answer

B) $\mathrm{LiAlH_4}$

Question 11

A student wants to synthesize 2-methyl-2-butanol from 2-methyl-2-butene. Which reagent should be used?

A) $\mathrm{H_2O, H_2SO_4}$ 
B) $\mathrm{BH_3 \cdot THF, H_2O_2, OH^-}$ 
C) $\mathrm{NaBH_4}$ 
D) $\mathrm{KMnO_4}$

Accepted Answer

A) $\mathrm{H_2O, H_2SO_4}$

Question 12

Which of the following is the product of the reaction of cyclopentanone with $\mathrm{CH_3MgBr}$ (excess)?

A) Cyclopentanol 
B) 1-Methylcyclopentanol 
C) 2-Methylcyclopentanol 
D) Cyclopentanone

Accepted Answer

B) 1-Methylcyclopentanol

Question 13

Which of the following reactions will convert a primary alkyl halide to a nitrile?

A) $\mathrm{NaCN}$ 
B) $\mathrm{NaOH}$ 
C) $\mathrm{HBr}$ 
D) $\mathrm{LiAlH_4}$

Accepted Answer

A) $\mathrm{NaCN}$

Question 14

Which of the following is the preferred product when 1-hexene is treated with $\mathrm{O_3}$ followed by $\mathrm{Zn, H_2O}$?

A) Hexanoic acid 
B) 1-Hexanol 
C) Hexanal and propanal 
D) 1,6-Hexanediol

Accepted Answer

C) Hexanal and propanal

Question 15

Which of the following is the correct IUPAC name for the compound shown below?

A cyclohexane ring with an OH group attached.

Accepted Answer

A) Cyclohexanol

Question 16

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

A) $\mathrm{NaBH_4}$ 
B) $\mathrm{KMnO_4}$ 
C) $\mathrm{H_2SO_4}$ 
D) $\mathrm{Br_2}$

Accepted Answer

A) $\mathrm{NaBH_4}$

Question 17

Which of the following is the major product when 1-pentene is treated with $\mathrm{Br_2}$ in $\mathrm{CH_2Cl_2}$?

A) 1,2-Dibromopentane 
B) 1-Bromopentane 
C) 2-Bromopentane 
D) Pentane

Accepted Answer

A) 1,2-Dibromopentane

Question 18

Which of the following is the preferred product when 1-butyne is treated with $\mathrm{H_2}$ and Lindlar's catalyst?

A) trans-2-Butene 
B) cis-2-Butene 
C) 1-Butene 
D) Butane

Accepted Answer

B) cis-2-Butene

Question 19

Which of the following is the major product when 1-pentene is treated with $\mathrm{OsO_4}$ followed by $\mathrm{NaHSO_3}$?

A) 1,2-Pentanediol 
B) 1-Pentanol 
C) 2-Pentanol 
D) Pentane

Accepted Answer

A) 1,2-Pentanediol

Organic Chemistry Exam Study Guide: Structure, Reactivity, and Synthesis

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