Q: Which of the following is the correct order of alkene stability (least stable to most stable) for the following: cyclopentene, 1-methylcyclopentene, 1,2-dimethylcyclopentene, 1,3-dimethylcyclopentene?

Cyclopentene < 1-methylcyclopentene < 1,2-dimethylcyclopentene < 1,3-dimethylcyclopentene

Q: Which of the following is a common misconception about the use of PCC in organic synthesis?

PCC can oxidize primary alcohols to carboxylic acids

Q: Which of the following statements about $S_N1$ reactions is TRUE?

Tertiary alkyl halides react faster than primary alkyl halides

Question 1

Which of the following functional groups is NOT present in the structure of levonorgestrel shown in the exam?

Accepted Answer

Carboxylic acid

Question 2

Rank the following alkyl halides in order of increasing $S_N1$ reactivity (1 = least reactive, 4 = most reactive): $\mathrm{CH_3CH_2Br}$, $\mathrm{(CH_3)_2CHBr}$, $\mathrm{(CH_3)_3CBr}$, $\mathrm{CH_3CH_2CH_2Br}$. Which is the most reactive?

Accepted Answer

$\mathrm{(CH_3)_3CBr}$

Question 3

Which reagent would best convert a primary alcohol to a primary alkyl chloride?

Accepted Answer

$\mathrm{SOCl_2}$

Question 4

In the reaction sequence: $\mathrm{1)\ NBS\ /\ hv\ \rightarrow\ 2)\ H_2O\ /\ \Delta}$, what is the role of NBS?

Accepted Answer

It brominates the benzylic position

Question 5

Which of the following is the correct IUPAC name for the compound shown as (E)-4-Fluoro-2-Hexene?

Accepted Answer

4-Fluorohex-2-ene

Question 6

Which of the following reagents would oxidize a secondary alcohol to a ketone without over-oxidation?

Accepted Answer

$\mathrm{PCC}$

Question 7

A student wants to synthesize cyclohexanone from cyclohexanol. Which reagent should they use?

Accepted Answer

$\mathrm{PCC}$

Question 8

Which of the following is the best method to convert 1-bromopropane to 1-propyl tosylate?

Accepted Answer

React 1-propanol with TsCl and pyridine

Question 9

Which of the following is the correct sequence of reagents to convert cyclopentanol to cyclopentyl chloride?

Accepted Answer

$\mathrm{SOCl_2}$

Question 10

In the reaction of 1-bromo-2,2-dimethylpropane with methanol, what is the major product?

Accepted Answer

2,2-Dimethylpropyl bromide

Question 11

Which of the following is the correct order of alkene stability (least stable to most stable) for the following: cyclopentene, 1-methylcyclopentene, 1,2-dimethylcyclopentene, 1,3-dimethylcyclopentene?

Accepted Answer

Cyclopentene < 1-methylcyclopentene < 1,2-dimethylcyclopentene < 1,3-dimethylcyclopentene

Question 12

Which of the following is a common misconception about the use of PCC in organic synthesis?

Accepted Answer

PCC can oxidize primary alcohols to carboxylic acids

Question 13

Which of the following reactions would best convert a benzyl bromide to a benzyl alcohol?

Accepted Answer

React with $\mathrm{H_2O}$

Question 14

Which of the following is the correct reagent to convert an aldehyde to a primary alcohol?

Accepted Answer

$\mathrm{NaBH_4}$

Question 15

In the total synthesis of cyclohexylacetonitrile from cyclohexane and ethyl bromide, which step introduces the nitrile group?

Accepted Answer

Reaction with $\mathrm{NaCN}$

Question 16

Which of the following statements about $S_N1$ reactions is TRUE?

Accepted Answer

Tertiary alkyl halides react faster than primary alkyl halides

Question 17

Which of the following is the correct product when 2-methyl-2-butanol is treated with $\mathrm{SOCl_2}$?

Accepted Answer

2-Chloro-2-methylbutane

Question 18

Which of the following is the best method to convert cyclohexanol to cyclohexanone?

Accepted Answer

Oxidation with $\mathrm{PCC}$

Question 19

Which of the following is the correct product when 4-methoxybenzyl bromide is treated with $\mathrm{NaOH}$?

Accepted Answer

4-Methoxybenzyl alcohol

Organic Chemistry: Functional Groups, Reactivity, Stability, and Synthesis

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