Question 1

Which of the following molecules is expected to be most soluble in water?

Accepted Answer

Methanol

Question 2

Which hybridization is present in the central carbon atom of ethyne ($C_2H_2$)?

Accepted Answer

$sp$

Question 3

Which of the following statements best explains why acetic acid ($CH_3COOH$) is more acidic than ethanol ($CH_3CH_2OH$)?

Accepted Answer

The carboxylate ion formed after deprotonation is stabilized by resonance.

Question 4

Which of the following is NOT a valid resonance structure for the acetate ion ($CH_3COO^-$)?

Accepted Answer

The negative charge is on the methyl group.

Question 5

Which of the following cyclohexane conformations is the most stable?

Accepted Answer

Chair

Question 6

A molecule of methylcyclohexane is placed in a solution. Which conformation will the methyl group prefer to occupy for maximum stability?

Accepted Answer

Equatorial position in the chair conformation

Question 7

Which of the following is a constitutional isomer of $C_4H_{10}$?

Accepted Answer

2-methylpropane

Question 8

How many unique $^{1}H$ NMR signals would you expect for ethyl acetate ($CH_3COOCH_2CH_3$)?

Accepted Answer

4

Question 9

Which of the following functional groups would show a signal near $
u = 1700$ cm$^{-1}$ in an IR spectrum?

Accepted Answer

Carboxylic acid

Question 10

Which of the following statements about $^{1}H$ NMR integration is correct?

Accepted Answer

Integration indicates the number of protons responsible for each signal.

Question 11

Which of the following compounds will have the highest number of $^{1}H$ NMR signals?

Accepted Answer

1,2-dichloroethane

Question 12

Which of the following best describes the difference between a constitutional isomer and a conformational isomer?

Accepted Answer

Constitutional isomers have different connectivity; conformational isomers differ by rotation around single bonds.

Question 13

Which of the following statements about hybridization is correct?

Accepted Answer

An $sp^2$ hybridized carbon has one unhybridized $p$ orbital.

Question 14

Which of the following molecules is expected to be the strongest acid?

Accepted Answer

Trifluoroacetic acid ($CF_3COOH$)

Question 15

Which of the following best explains why cyclohexane adopts a chair conformation?

Accepted Answer

To minimize torsional and steric strain.

Question 16

Which of the following is true about the number of $^{1}H$ NMR signals for 2-butanol ($CH_3CH(OH)CH_2CH_3$)?

Accepted Answer

There are 4 signals.

Question 17

Which of the following is a correct statement about the integration of $^{1}H$ NMR signals for tert-butyl alcohol ($C(CH_3)_3OH$)?

Accepted Answer

The methyl protons integrate to 9.

Question 18

Which of the following is the correct order of acidity (most acidic to least acidic)?

Accepted Answer

Acetic acid > Phenol > Ethanol

Question 19

Which of the following statements about the boat conformation of cyclohexane is correct?

Accepted Answer

It has more steric strain than the chair conformation.

Question 20

Which of the following best describes the splitting pattern for the methylene protons ($CH_2$) in ethyl bromide ($CH_3CH_2Br$) in $^{1}H$ NMR?

Accepted Answer

Quartet

Organic Chemistry Study Guide: Solubility, Acidity, Cyclohexane Conformations, and NMR

Study Guide - Practice Questions