Question 1

Which of the following compounds is classified as a cyanohydrin?

Accepted Answer

A molecule containing both a cyano group ($$-CN) $$and a hydroxyl group ($$-OH) $$attached to the same carbon.

Question 2

Which of the following is the correct product of the reaction of benzene with $$SO_3$$ and $$H_2SO_4$$ under heat?

Accepted Answer

Benzenesulfonic acid ($$C_6H_5SO_3H)$$

Question 3

Which compound is more reactive toward nucleophilic attack: acetone ($$CH_3COCH_3) or $$trifluoroacetone ($$CF_3COCH_3$$)?

Accepted Answer

Trifluoroacetone ($$CF_3COCH_3)$$

Question 4

Which of the following is the correct mechanism for the acid-catalyzed hydrolysis of an acetal?

Accepted Answer

Protonation of the acetal oxygen, followed by nucleophilic attack by water, formation of a hemiacetal, and subsequent loss of an alcohol to yield the carbonyl compound.

Question 5

Which of the following reactions is an example of Friedel–Crafts alkylation?

Accepted Answer

$$C_6H_5CN + RCl \xrightarrow{$$AlCl_3$$} C_6H_5CR$$

Question 6

Which of the following is the major product when ethyl benzoate is treated with DIBAL-H followed by water?

Accepted Answer

Benzaldehyde ($$C_6H_5CHO)$$

Question 7

Which of the following statements best explains why $$CF_3-$$substituted benzene is less reactive toward electrophilic aromatic substitution than $$F-$$substituted benzene?

Accepted Answer

$$CF_3 is a $$strong electron-withdrawing group by induction and resonance, deactivating the ring more than $$F.$$

Question 8

Which of the following is the correct product of the side-chain oxidation of toluene ($$C_6H_5CH_3) $$with $$KMnO_4$$, $$NaOH$$, and heat followed by acid workup?

Accepted Answer

Benzoic acid ($$C_6H_5COOH)$$

Question 9

Which of the following is a correct resonance structure for the intermediate formed during electrophilic aromatic substitution of benzene?

Accepted Answer

A carbocation delocalized over three adjacent carbons of the benzene ring.

Question 10

Which of the following is the correct product when cyclopentanone is treated with $$H_2O$$ and $$H^+$$?

Accepted Answer

Cyclopentanone hydrate (geminal diol)

Question 11

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

$$\mathrm{CH_3COOCH_2CH_3}$$

Accepted Answer

Ethyl acetate

Question 12

Which of the following is the correct product when benzene is treated with $$Br_2$$ and light?

Accepted Answer

Bromobenzene ($$C_6H_5Br)$$

Question 13

Which of the following is the correct product when benzyl bromide ($$C_6H_5CH_2Br) is $$treated with $$PPh_3$$?

Accepted Answer

Benzyltriphenylphosphonium bromide ($$C_6H_5CH_2PPh_3Br)$$

Question 14

Which of the following is the correct product when $$t-$$BuOK is reacted with benzyltriphenylphosphonium bromide and acetone?

Accepted Answer

1-Phenyl-2-methylpropene (Wittig product)

Question 15

Which of the following is the correct name for the cyclic form of deoxyribose with the configuration $$3S, 4R$$?

Accepted Answer

A specific stereoisomer of deoxyribofuranose

Question 16

Which of the following is the correct product when a nitrile ($$R-CN) is $$treated with $$H_2O$$, $$H^+$$, and heat?

Accepted Answer

Carboxylic acid ($$R-COOH)$$

Question 17

Which of the following is the correct product when an acetal is hydrolyzed under acidic conditions?

Accepted Answer

A carbonyl compound and two alcohols

Question 18

Which of the following is the correct product when a carboxylic acid is treated with $$Cl_2$$ and $$AlCl_3$$?

Accepted Answer

Chlorobenzoic acid (chlorination at the meta position)

Question 19

Which of the following is the correct product when a ketone is treated with $$NaOH$$ and $$H_2O$$?

Accepted Answer

A hydrate (geminal diol)

Organic Chemistry II: Functional Groups, Reactivity, Mechanisms, and Stereochemistry – Study Notes

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