Question 1

Which of the following correctly describes the product of the reaction of 2-butyne with $\mathrm{H_2}$ and Lindlar catalyst?

Accepted Answer

cis-2-butene

Question 2

What is the IUPAC name for the following compound?

$\mathrm{CH_3CH_2CH(CH_3)CH_2CH_3}$

Accepted Answer

3-methylpentane

Question 3

Which reagent would convert cyclohexanol to cyclohexene in a single step?

Accepted Answer

$\mathrm{POCl_3}$, pyridine

Question 4

Which of the following statements about MCPBA (meta-chloroperoxybenzoic acid) is correct?

Accepted Answer

It converts alkenes to epoxides via syn addition.

Question 5

A reaction sequence converts 1-butyne to 2-butanone. Which set of reagents would accomplish this transformation?

Accepted Answer

1) $\mathrm{HgSO_4}$, $\mathrm{H_2SO_4}$, $\mathrm{H_2O}$

Question 6

Which of the following best describes the stereochemical outcome of the reaction of cyclohexene with $\mathrm{Br_2}$ in water?

Accepted Answer

Trans-1,2-bromohydrin is formed due to anti addition.

Question 7

Which of the following is the correct product for the reaction:

$\mathrm{1-butyne}$ + $\mathrm{NaNH_2}$, then $\mathrm{CH_3CH_2Br}$?

Accepted Answer

2-pentyne

Question 8

How many stereoisomers are possible for a compound with 3 asymmetric centers and no plane of symmetry?

Accepted Answer

$8$

Question 9

Which of the following statements about the reaction of an alkyne with $\mathrm{HBr}$ (1 equivalent) is correct?

Accepted Answer

The product is a vinyl bromide with Markovnikov regioselectivity.

Question 10

Which of the following best explains why the equatorial methyl group in methylcyclohexane is more stable than the axial methyl group?

Accepted Answer

Axial methyl groups experience 1,3-diaxial interactions, increasing steric strain.

Question 11

Which of the following reagents would convert a primary alcohol to an alkyl bromide?

Accepted Answer

$\mathrm{PBr_3}$

Question 12

What is the relationship between the following two compounds?

$\mathrm{(R,R)-2,3-dibromobutane}$ 	ext{ and } $\mathrm{(S,S)-2,3-dibromobutane}$

Accepted Answer

They are enantiomers.

Question 13

Which of the following is the correct product for the reaction of 1,2-dimethylcyclohexanol with $\mathrm{POCl_3}$ and pyridine?

Accepted Answer

1,2-dimethylcyclohexene

Question 14

Which of the following best describes the product of the reaction of 1,3-butadiene with $\mathrm{HBr}$ (1 equivalent) at low temperature?

Accepted Answer

1,2-addition product

Question 15

Which of the following is the correct sequence of reagents to convert 1-butyne to butanal?

Accepted Answer

1) $\mathrm{(Sia)_2BH}$ 2) $\mathrm{H_2O_2}$, $\mathrm{NaOH}$

Question 16

Which of the following best describes the product of the reaction of 1,2-dibromocyclohexane with $\mathrm{NaNH_2}$?

Accepted Answer

Cyclohexene with a triple bond (cyclohexyne)

Question 17

Which of the following is the correct product for the reaction of 1,2-dimethylcyclohexanol with $\mathrm{H_2SO_4}$ and heat?

Accepted Answer

1,2-dimethylcyclohexene

Question 18

Which of the following best describes the product of the reaction of 1,2-dibromocyclohexane with $\mathrm{NaNH_2}$ followed by $\mathrm{CH_3CH_2Br}$?

Accepted Answer

Ethylcyclohexyne

Question 19

Which of the following is the correct product for the reaction of 1,2-dimethylcyclohexanol with $\mathrm{NaOCl}$ and acetic acid?

Accepted Answer

1,2-dimethylcyclohexanone

CHEM 2400 Final Exam Study Guide: Organic Chemistry II Core Concepts and Applications

Study Guide - Practice Questions