Question 1

Which of the following best describes the functional group present in the compound shown below?

$$\mathrm{Ph{-}CO{-}NH_2$}$$

Accepted Answer

Amide

Question 2

What is the IUPAC name for the following compound?

$$\mathrm{CH_3${-}CH_2${-}CHBr{-}CH_2${-}CH_3$}$$

Accepted Answer

3-bromopentane

Question 3

Which reagent would you use to convert a primary alcohol to an alkyl chloride?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$

Question 4

A reaction of 1-butyne with $$\mathrm{1. BH_3$, THF}$$ followed by $$\mathrm{2. H_2O_2, NaOH, H_2O}$$ yields which major product?

Accepted Answer

Butanal (from anti-Markovnikov hydration, enol tautomerizes to aldehyde)

Question 5

Which of the following sequences would best achieve the transformation of an alkene to a vicinal dibromide?

Accepted Answer

Br$$_2$$, CCl$$_4$$

Question 6

What is the product of the following reaction?

$$\mathrm{Cyclohexene + H_2SO_4, H_2O}$$

Accepted Answer

Cyclohexanol

Question 7

Which of the following best explains the regioselectivity observed in the hydroboration-oxidation of alkenes?

Accepted Answer

The boron atom adds to the less substituted carbon due to both steric and electronic effects, resulting in anti-Markovnikov addition.

Question 8

Which of the following is the correct order of stability for the following radicals?

$$\mathrm{CH_3$\cdot}$$, $$\mathrm{CH_2$=CH\cdot}$$, $$\mathrm{$$PhCH_2$$\cdot}$$, $$\mathrm{(CH_3$)_3C\cdot}$$

Accepted Answer

$$\mathrm{$$PhCH_2$$\cdot \u003e (CH_3$)_3C\cdot \u003e CH_2$=CH\cdot \u003e CH_3$\cdot}$$

Question 9

Which of the following reagents would you use to reduce an alkyne to a trans-alkene?

Accepted Answer

$$\mathrm{Na, NH_3$ (liq)}$$

Question 10

Which of the following best describes the product of the reaction of 1-methylcyclohexene with $$\mathrm{Br_2$, H_2O}$$?

Accepted Answer

Trans-1-bromo-2-methylcyclohexanol

Question 11

A retrosynthetic analysis of a target molecule reveals the need for a Grignard reagent. Which of the following is a correct statement about the preparation of a Grignard reagent?

Accepted Answer

It is prepared by reacting an alkyl halide with magnesium metal in dry ether.

Question 12

Which of the following best describes the mechanism of acid-catalyzed hydration of an alkene?

Accepted Answer

The reaction proceeds via a carbocation intermediate, following Markovnikov's rule.

Question 13

Which of the following is the correct product for the reaction of 2-methyl-2-butene with $$\mathrm{HBr} in $$the presence of peroxides ($$\mathrm{ROOR}$$)?

Accepted Answer

1-bromo-2-methylbutane

Question 14

Which of the following best explains why tertiary carbocations are more stable than secondary or primary carbocations?

Accepted Answer

Tertiary carbocations are stabilized by hyperconjugation and inductive effects from three alkyl groups.

Question 15

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

Accepted Answer

$$\mathrm{$$NaBH_4$$}$$

Question 16

Which of the following is the correct product for the reaction of benzene with $$\mathrm{Br_2$} in $$the presence of $$\mathrm{$$FeBr_3$$}$$?

Accepted Answer

Bromobenzene

Question 17

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

Accepted Answer

1-hexyne

Question 18

Which of the following is the correct order of stability for the following alkenes?

$$\mathrm{CH_2$=CH_2$}$$, $$\mathrm{CH_2$=$$CHCH_3$$}$$, $$\mathrm{(CH_3$)_2C=CH_2$}$$, $$\mathrm{(CH_3$)_2C=CH(CH_3$)}$$

Accepted Answer

$$\mathrm{(CH_3$)_2C=CH(CH_3$) \u003e (CH_3$)_2C=CH_2$ \u003e CH_2$=$$CHCH_3$$ \u003e CH_2$=CH_2$}$$

Question 19

Which of the following best describes the product of the reaction of cyclohexene with $$\mathrm{$$OsO_4$$}$$ followed by $$\mathrm{$$NaHSO_3$$, H_2O}$$?

Accepted Answer

cis-1,2-cyclohexanediol

Organic Chemistry II: Functional Groups, Nomenclature, and Reaction Mechanisms – Exam Study Guide

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