Question 1

Which of the following correctly names the compound with the structure: $$\mathrm{CH_3CH_2CH(CH_3$)CH_2CH_3}$$, and assigns the correct R/S configuration at the stereocenter?

Accepted Answer

3-methylpentane, (R)

Question 2

Which of the following reagents would convert a terminal alkyne to a cis-alkene?

Accepted Answer

$$\mathrm{H_2$,\ Lindlar\ catalyst}$$

Question 3

What is the product of the following reaction sequence?

$$\mathrm{Cyclohexene\xrightarrow{MCPBA,\ DCM}}$$

Accepted Answer

Cyclohexene oxide (epoxide)

Question 4

Which of the following statements about the reaction of 1-butyne with $$\mathrm{$$NaNH_2$$}$$ followed by $$\mathrm{CH_3CH_2Br} is $$correct?

Accepted Answer

It produces 1-pentyne.

Question 5

Which of the following best describes the stereochemical outcome of the hydroboration-oxidation of 1-methylcyclohexene?

Accepted Answer

Anti-Markovnikov addition, syn addition of H and OH

Question 6

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

$$\mathrm{\begin{array}{l} 	ext{Cyclohexane ring with a Br at C1 and a Cl at C3 (cis to each other)} \end{array}}$$

Accepted Answer

cis-1-bromo-3-chlorocyclohexane

Question 7

Which of the following statements about the reaction of 2-butyne with $$\mathrm{H_2$}$$ and Lindlar catalyst is correct?

Accepted Answer

It produces cis-2-butene.

Question 8

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

Accepted Answer

8

Question 9

Which of the following best describes the product of the reaction: $$\mathrm{1,2-dibromocyclohexane\xrightarrow{$$NaNH_2$$,\ NH_3$}}$$?

Accepted Answer

Cyclohexyne

Question 10

Which of the following is the most stable conformation for cis-1,3-dimethylcyclohexane?

Accepted Answer

One methyl axial, one methyl equatorial

Question 11

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

Accepted Answer

$$\mathrm{PCC}$$

Question 12

Which of the following is the correct product for the reaction: $$\mathrm{1-methylcyclohexanol\xrightarrow{$$POCl_3$$,\ pyridine}}$$?

Accepted Answer

1-methylcyclohexene

Question 13

Which of the following best describes the relationship between the following two compounds?

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

Accepted Answer

Enantiomers

Question 14

Which of the following is the correct sequence of reagents to convert 1-butyne to trans-2-butene?

Accepted Answer

$$\mathrm{Na,\ NH_3$}$$

Question 15

Which of the following is the correct product for the reaction: $$\mathrm{Cyclohexanol\xrightarrow{H_2SO_4,\ \Delta}}$$?

Accepted Answer

Cyclohexene

Question 16

Which of the following best describes the product of the reaction: $$\mathrm{1,2-dibromopropane\xrightarrow{$$NaNH_2$$}}$$?

Accepted Answer

Propyne

Question 17

Which of the following is the correct IUPAC name for the compound: $$\mathrm{(Z)-3-iodohex-2-ene}$$?

Accepted Answer

(Z)-3-iodohex-2-ene

Question 18

Which of the following statements is true regarding the reaction of 1-methylcyclohexene with $$\mathrm{Br_2$,\ $$CCl_4$$}$$?

Accepted Answer

It produces a trans-1,2-dibromide via anti addition.

Question 19

Which of the following best describes the product of the reaction: $$\mathrm{Cyclohexanol\xrightarrow{PCC}}$$?

Accepted Answer

Cyclohexanone

Question 20

Which of the following is the correct relationship between the following two compounds?

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

Accepted Answer

Diastereomers

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

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