Question 1

Which of the following correctly arranges the nucleophiles in order of increasing nucleophilicity?

Accepted Answer

CH3OH \u003c CH3CO2- \u003c CH3O-

Question 2

Which of the following alkyl bromides is most reactive in an $$S_N2$$ reaction?

Accepted Answer

CH3CH2CH2Br

Question 3

What is the best way to describe the stereochemistry of the double bond indicated in the compound below?

$$\mathrm{Cl}-\mathrm{C}=\mathrm{C}-\mathrm{CH}_2-\mathrm{C}(\mathrm{CH}_3)_3$$

with $$\mathrm{CH}_3$$ and $$\mathrm{CH}_2-\mathrm{CH}=\mathrm{CH}_2 as $$the other substituents.

Accepted Answer

E

Question 4

Which alkyl halide is expected to react the fastest in an $$S_N1$$ reaction?

Accepted Answer

($$CH_3)_3$$CBr

Question 5

In the E2 elimination of 2-bromobutane, which conformation leads directly to the formation of cis-2-butene?

Accepted Answer

Conformation (b)

Question 6

Which of the following statements about the E2 elimination shown below is correct?

$$\mathrm{R} = -\mathrm{CH}_2\mathrm{CH}_3 or$$ $$-\mathrm{C}(\mathrm{CH}_3)_3$$

Accepted Answer

The II:I ratio is greater when R = -tert-butyl than when R = -ethyl

Question 7

Assuming no other changes, how would the rate be affected if the concentration of both 2-chloro-2-methylpentane and sodium iodide were simultaneously doubled in an $$S_N2$$ reaction?

Accepted Answer

It would quadruple the rate.

Question 8

What is the relationship between the following two molecules?

$$\mathrm{Br}-\mathrm{C}_2\mathrm{H}_4-\mathrm{Cl}$$ and $$\mathrm{Cl}-\mathrm{C}_2\mathrm{H}_4-\mathrm{Br} ($$with different spatial arrangements)

Accepted Answer

enantiomers

Question 9

Rank the following aromatic compounds in order of increasing stability:

A: ortho-methylbenzene
B: meta-methylbenzene
C: para-methylbenzene

Accepted Answer

B \u003c A \u003c C

Question 10

What is the major product of the following reaction?

Cyclohexylacetylene $$+\ \mathrm{HgSO}_4,\ \mathrm{H}_2\mathrm{SO}_4,\ \mathrm{H}_2\mathrm{O}$$

Accepted Answer

Cyclohexyl methyl ketone

Question 11

What is the product of the hydroboration-oxidation of cyclobutylacetylene using $$\mathrm{Sia}_2\mathrm{BH}$$ followed by $$\mathrm{H}_2\mathrm{O}_2,\ \mathrm{OH}^-$$?

Accepted Answer

Cyclobutyl aldehyde

Question 12

What is the product of ozonolysis of methylcyclohexene?

Accepted Answer

A six-membered ring with a methyl ketone and an aldehyde

Question 13

Which of the following best describes the mechanism for the reaction of 1-bromo-2,2-dimethylcyclopentane with ethanol to form a cyclopentene derivative?

Accepted Answer

E1 elimination

Question 14

Which of the following is the major product of the reaction of 4-penten-1-ol with $$\mathrm{Br}_2$$?

Accepted Answer

A brominated tetrahydrofuran ring

Question 15

Which of the following best describes the type of reaction occurring when an amine and a trifluoroalkene are heated together?

Accepted Answer

Diels-Alder cycloaddition

Organic Chemistry I Final Exam Study Guidance

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