Question 1

Which of the following statements about the IUPAC naming of cycloalkanes is correct?

Accepted Answer

When naming cycloalkanes, the ring is named as the parent hydrocarbon unless a substituent has more carbons than the ring.

Question 2

Which conformation of cyclohexane is generally the most stable, and why?

Accepted Answer

Chair, because it minimizes both angle and torsional strain.

Question 3

In a Newman projection of ethane, which conformation is lowest in energy and why?

Accepted Answer

Staggered, because it minimizes electron repulsion between bonds.

Question 4

Which of the following carbocations is the most stable?

Accepted Answer

$(CH_3)_3C^+$

Question 5

Which of the following alkenes is the most stable?

Accepted Answer

$(CH_3)_2C=CH(CH_3)$

Question 6

During the acid-catalyzed hydration of 2-methylpropene, which product is formed according to Markovnikov's rule?

Accepted Answer

2-methyl-2-propanol

Question 7

Which of the following best describes the outcome of ozonolysis of cyclohexene?

Accepted Answer

It cleaves the double bond to form two molecules of glutaraldehyde.

Question 8

Which of the following statements about electrophilic aromatic substitution (EAS) is correct?

Accepted Answer

Ortho and para positions are favored by electron-donating groups.

Question 9

Which of the following is a correct application of Huckel's rule for aromaticity?

Accepted Answer

A compound is aromatic if it contains $4n+2$ pi electrons, where $n$ is an integer.

Question 10

Which of the following best describes a meso compound?

Accepted Answer

A compound with chiral centers and an internal plane of symmetry, making it achiral.

Question 11

Which of the following statements about SN2 reactions is correct?

Accepted Answer

The reaction proceeds with inversion of configuration at the stereocenter.

Question 12

Which of the following is the best leaving group for an SN1 reaction?

Accepted Answer

$H_2O$

Question 13

Which of the following statements about the Zaitsev rule is correct?

Accepted Answer

The most substituted alkene is the major product in elimination reactions.

Question 14

Which reagent would you use to convert a primary alcohol to an alkyl chloride?

Accepted Answer

$SOCl_2$

Question 15

Which of the following is a correct statement about the Grignard reaction with a ketone?

Accepted Answer

It produces a tertiary alcohol after hydrolysis.

Question 16

Which of the following reagents can reduce a carboxylic acid to a primary alcohol?

Accepted Answer

$LiAlH_4$

Question 17

Which of the following best describes the Fischer esterification reaction?

Accepted Answer

An acid-catalyzed reaction between a carboxylic acid and an alcohol to form an ester.

Question 18

Which of the following is the correct product of the Williamson ether synthesis between sodium ethoxide and 1-bromopropane?

Accepted Answer

Ethyl propyl ether

Question 19

Which of the following best describes the function of an acetal protecting group in organic synthesis?

Accepted Answer

It protects carbonyl groups from nucleophilic attack.

Organic Chemistry Core Concepts: Structured Study Notes

Study Guide - Practice Questions