Question 1

Which of the following hydrogens in acetic acid is the most acidic?

Accepted Answer

The hydrogen attached to the carboxyl group ($$\mathrm{COOH})$$

Question 2

Which reaction below is the best synthesis of 2,2-dibromopropane?

Accepted Answer

Addition of $$\mathrm{Br_2$} to $$propanone

Question 3

What is the major product of the following reaction: $$\mathrm{CH_3CH_2Br}$$ + $$\mathrm{NaOH} ($$ethanol, heat)?

Accepted Answer

$$\mathrm{CH_2$=CH_2$}$$

Question 4

Which of the following is the best explanation for why pentan-1-ol is more reactive than 3-methylpentan-3-ol in oxidation reactions?

Accepted Answer

Primary alcohols are oxidized more easily than tertiary alcohols due to less steric hindrance

Question 5

Which of the following alkenes will yield a racemic mixture upon reaction with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

2-methyl-2-butene

Question 6

Which reagent would you use to convert cyclohexene to cyclohexane?

Accepted Answer

$$\mathrm{H_2$}$$, Pd/C

Question 7

What is the product of the reaction between 1-chloro-6-methylhexane and sodium ethoxide in ethanol at room temperature?

Accepted Answer

6-methylhexyl ethyl ether

Question 8

Which of the following best describes the mechanism of the $$\mathrm{S_N2}$$ reaction?

Accepted Answer

A concerted one-step mechanism with simultaneous bond breaking and forming

Question 9

Which of the following compounds is a pyridinium bromide?

Accepted Answer

$$\mathrm{C_5H_5NBr}$$

Question 10

Which of the following is the correct structure for (2E, 4E, 5-trans)-2-chloro-4-(1,1-dimethylethyl)-6-methylhexa-2,3-diene?

Accepted Answer

A hexadiene with chlorine at C2, tert-butyl at C4, methyl at C6, and trans double bonds at C2 and C4

Question 11

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

Accepted Answer

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

Question 12

What is the major product when 2-methyl-2-butene reacts with $$\mathrm{HBr}$$?

Accepted Answer

2-bromo-2-methylbutane

Question 13

Which of the following best explains why $$\mathrm{$$NaBH_4$$} is $$selective for reducing aldehydes and ketones but not esters?

Accepted Answer

Esters are less electrophilic than aldehydes and ketones

Question 14

Which of the following is the correct intermediate in the $$\mathrm{S_N1}$$ reaction of tert-butyl bromide?

Accepted Answer

A tert-butyl carbocation ($$\mathrm{(CH_3$)_3C^+})$$

Question 15

Which of the following reagents would you use to convert an alkene to a vicinal diol?

Accepted Answer

$$\mathrm{$$OsO_4$$}$$, $$\mathrm{H_2O_2}$$

Question 16

Which of the following is the best method to confirm the presence of the product in an organic reaction?

Accepted Answer

Infrared spectroscopy (IR)

Question 17

Which of the following is the correct stepwise mechanism for the acid-catalyzed hydration of 2-methylpropene?

Accepted Answer

Protonation of the alkene, formation of carbocation, nucleophilic attack by water, deprotonation

Question 18

Which of the following is the correct product for the reaction of cyclohexene with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

trans-1,2-dibromocyclohexane

Question 19

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

Accepted Answer

$$\mathrm{PCC} ($$Pyridinium chlorochromate)

Organic Chemistry 907: Exam Study Guide – Reaction Mechanisms, Synthesis, and Structure

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