Question 1

Which of the following bonds has the highest polarity?

Accepted Answer

$\mathrm{C-Cl}$$

Question 2

What is the hybridization of the carbon atom in ethyne ($$\mathrm{CH\equiv CH}$$)?

Accepted Answer

$$sp$$

Question 3

Which functional group is present in the following structure: $$\mathrm{CH_3COOH}$$?

Accepted Answer

Carboxylic acid

Question 4

What is the IUPAC name for the following compound?

$$\mathrm{CH_3CH_2CH_2CH_2OH}$$

Accepted Answer

Butan-1-ol

Question 5

Which of the following is the most stable conformation for 1-ethyl-3-methylcyclohexane?

Accepted Answer

Both ethyl and methyl groups in equatorial positions

Question 6

Which of the following is the strongest acid?

Accepted Answer

Carboxylic acid

Question 7

What is the relationship between the following two molecules?

(Structures: both are cis-1,2-dimethylcyclohexane)

Accepted Answer

Identical

Question 8

Calculate the degree of unsaturation for a compound with formula $$\mathrm{C_6H_{10}}.$$

Accepted Answer

2

Question 9

Which reagent will convert an internal alkyne to a cis-alkene?

Accepted Answer

Lindlar's catalyst

Question 10

List the following carbocations in order of increasing stability: primary, secondary, tertiary, allylic.

Accepted Answer

Primary \u003c Secondary \u003c Tertiary \u003c Allylic

Question 11

Which product results from the $$\mathrm{S_N2}$$ reaction between $$(R)-2-$$bromopentane and hydroxide ion, $$\mathrm{OH^-}$$?

Accepted Answer

Inversion product, $$(S)-2-$$pentanol

Question 12

Which halide reacts most rapidly via an $$\mathrm{S_N1}$$ mechanism?

Accepted Answer

Tertiary alkyl halide

Question 13

What is the major product of the following E2 reaction?

$$\mathrm{CH_3CH_2CH_2Br}$$ + $$\mathrm{NaOEt}$$ $$\rightarrow$$

Accepted Answer

$$\mathrm{CH_3CH=CH_2$}$$

Question 14

How can you synthesize an ether from an alcohol?

Accepted Answer

Williamson ether synthesis

Question 15

Which of the following is a termination step in a radical reaction?

Accepted Answer

$$\mathrm{Cl^\cdot + Cl^\cdot \rightarrow Cl_2$}$$

Question 16

What is the major product when cyclopentane is exposed to bromine under UV light?

Accepted Answer

Bromocyclopentane (bromine at a tertiary carbon)

Question 17

Which of the following reagents will convert a terminal alkyne to an alkene?

Accepted Answer

Lindlar's catalyst

Question 18

Which compound will undergo an $$\mathrm{S_N2}$$ reaction most easily?

Accepted Answer

1-bromobutane

Question 19

What is the product of the following reaction?

$$\mathrm{CH_3CH_2CH_2CH_2OH}$$ + $$\mathrm{HCl}$$ $$\rightarrow$$

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2Cl}$$

Question 20

Which of the following is the major product of the E2 reaction shown below?

$$\mathrm{CH_3CH_2CH_2CH_2Br}$$ + $$\mathrm{NaOEt}$$ $$\rightarrow$$

Accepted Answer

$$\mathrm{CH_3CH_2CH=CH_2$}$$

Organic Chemistry I Final Review: Key Concepts and Mechanisms

Study Guide - Practice Questions