Question 1

What is the systematic IUPAC name for the compound shown below?

$$\mathrm{CH_3CH(Br)CH_2CHO}$$

Accepted Answer

2-bromobutanal

Question 2

What is the systematic IUPAC name for the following compound?

$$\mathrm{CH_3CH_2COCH(CH_3$)CH_2CH_3}$$

Accepted Answer

5-methyl-3-hexanone

Question 3

Which of the following structures represents cyclohexanone?

Accepted Answer

V

Question 4

What is the systematic IUPAC name for the compound below?

$$\mathrm{CH_3C(=O)CH_2CH(CH_3$)CH(CH_3$)Cl}$$

Accepted Answer

5-chloro-3-methyl-2-hexanone

Question 5

What is the systematic IUPAC name for the following carboxylic acid?

$$\mathrm{CH_3CH_2CH(CH_3$)CH_2COOH}$$

Accepted Answer

3-methylpentanoic acid

Question 6

What is the common name of the following compound?

$$\mathrm{(HCO)_2O}$$

Accepted Answer

formic anhydride

Question 7

Which of the following structures is N,N-dimethylbenzamide?

Accepted Answer

V

Question 8

What is the systematic IUPAC name for the following compound?

$$\mathrm{(CH_3$)_2CHCH(Cl)CH_2CH_2COOH}$$

Accepted Answer

4-chloro-5-methylhexanoic acid

Question 9

What is the systematic IUPAC name for the following compound?

$$\mathrm{CH_3CH_2CH=C(CH_3$)COOH}$$

Accepted Answer

(E)-2-methyl-2-pentenoic acid

Question 10

What is the systematic IUPAC name for the following compound?

$$\mathrm{CH_3CH_2CH_2CH_2COCl}$$

Accepted Answer

pentanoyl chloride

Question 11

Which of the following best describes the main intermolecular force between two molecules of propanoic acid?

Accepted Answer

hydrogen bonding

Question 12

In a nucleophilic acyl substitution reaction, what is the key mechanistic step?

Accepted Answer

addition to the carbonyl by a nucleophile is followed by loss of the leaving group

Question 13

Acetyl chloride undergoes nucleophilic acyl substitution faster than methyl acetate because:

Accepted Answer

chloride ion is a better leaving group than methoxide ion

Question 14

Which of the following compounds will form acetic acid when hydrolyzed with acid and heat?

Accepted Answer

all of these

Question 15

Which of the following is the most reactive toward addition of a Grignard reagent?

Accepted Answer

I (aldehyde)

Question 16

Which of the following is the least reactive toward addition of a Grignard reagent?

Accepted Answer

V (amide)

Question 17

What kind of reactions do aldehydes and ketones typically undergo?

Accepted Answer

nucleophilic addition

Question 18

Why do aldehydes undergo nucleophilic addition reactions, whereas esters undergo nucleophilic acyl substitution reactions?

Accepted Answer

Once the nucleophile adds to an aldehyde, neither H$$^-$$ nor R$$^-$$ can be eliminated because they are strongly basic.

Question 19

Which of the following reactions can be used to prepare 3-methyl-3-hexanol?

Accepted Answer

A, B, and C

Question 20

Diisobutylaluminum hydride (DIBALH) can be used to carry out which of the following conversions?

Accepted Answer

ester to aldehyde

Systematic Naming and Identification of Organic Compounds

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