Question 1

Which of the following is NOT a nucleophile? Explain why.

Accepted Answer

$$\mathrm{CH_3Cl}$$

Question 2

Which factor would NOT increase the rate of an SN2 reaction?

Accepted Answer

Using a tertiary alkyl halide as the substrate

Question 3

What is the major product of the following reaction? $$\mathrm{C_6H_5CH_2Br}$$ + $$\mathrm{NaCN} (in $$ethanol)

Accepted Answer

$$\mathrm{C_6H_5CH_2CN}$$

Question 4

Which of the following statements about the SN1 reaction mechanism is TRUE?

Accepted Answer

A carbocation intermediate is formed.

Question 5

A student treats cyclohexene with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}. $$What is the major product?

Accepted Answer

1,2-dibromocyclohexane

Question 6

Which reagent would best convert a primary alcohol to an aldehyde?

Accepted Answer

$$\mathrm{PCC}$$

Question 7

What is the IUPAC name for the following compound: $$\mathrm{CH_3CH_2CH_2CH_2CH_2CH_2OH}$$?

Accepted Answer

1-Hexanol

Question 8

Which of the following is the best method to distinguish between an aldehyde and a ketone?

Accepted Answer

Reaction with Tollens' reagent

Question 9

A compound $$\mathrm{C_7H_8}$$ reacts with $$\mathrm{$$KMnO_4$$} to $$give $$\mathrm{C_7H_6O_2}. $$What is the original compound?

Accepted Answer

Toluene

Question 10

Which of the following is NOT a possible intermediate in the mechanism of electrophilic aromatic substitution?

Accepted Answer

A radical cation

Question 11

What is the major product when 2-bromopropane is treated with alcoholic $$\mathrm{KOH}$$?

Accepted Answer

Propene

Question 12

Which of the following statements about Grignard reagents is FALSE?

Accepted Answer

They are stable in the presence of moisture.

Question 13

What is the product of the reaction: $$\mathrm{CH_3COCl}$$ + $$\mathrm{CH_3CH_2OH} (in $$pyridine)?

Accepted Answer

$$\mathrm{CH_3COOCH_2CH_3}$$

Question 14

Which of the following is the correct order of reactivity towards nucleophilic substitution (SN2)?

Accepted Answer

Methyl \u003e Primary \u003e Secondary \u003e Tertiary

Question 15

A student oxidizes 2-butanol with $$\mathrm{K_2Cr_2O_7} in $$acid. What is the major product?

Accepted Answer

2-butanone

Question 16

Which of the following is the best description of the mechanism for the reaction of $$\mathrm{CH_3CH_2Br}$$ with $$\mathrm{OH^-} in $$water?

Accepted Answer

Bimolecular nucleophilic substitution (SN2)

Question 17

Which of the following is the major product when benzene reacts with $$\mathrm{CH_3Cl}$$ and $$\mathrm{$$AlCl_3$$}$$?

Accepted Answer

Toluene

Question 18

What is the major organic product when cyclohexanone is treated with $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

Cyclohexanol

Question 19

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

Accepted Answer

Protonation of ethene to form a carbocation, followed by nucleophilic attack by water, then deprotonation

Question 20

A compound $$\mathrm{C_4H_8Br_2} is $$treated with excess $$\mathrm{$$NaNH_2$$} in $$liquid ammonia. What is the major product?

Accepted Answer

Butyne

Organic Chemistry 907 - Homework Study Guide: Reaction Mechanisms, Synthesis, and Structure Elucidation

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