Question 1

Which of the following best describes the role of $$\mathrm{CH_3CH_2NH_2} in $$the reaction $$\mathrm{H_3C{-}NH_2$ + CH_3CH_2Cl \rightarrow CH_3NHCH_2CH_3 + Cl^-}$$?

Accepted Answer

It acts as the nucleophile by donating a lone pair to the carbon in $$\mathrm{CH_3CH_2Cl}.$$

Question 2

In the molecule below, how many carbon–carbon single bonds and how many carbon–carbon double bonds are present?

$$\mathrm{CH_2$=CH{-}CH_2${-}CH=CH_2$}$$

Accepted Answer

3 single bonds, 2 double bonds

Question 3

Which functional groups are present in the structure of Vildagliptin (shown below)?

$$\mathrm{\includegraphics[height=0.5in]{vildagliptin.png}}$$

Accepted Answer

Alcohol, amine, amide, aromatic ring

Question 4

Which of the following is a constitutional isomer of $$\mathrm{C_5H_{10}}$$?

Accepted Answer

Cyclopentane

Question 5

Which molecule has the higher boiling point and why?

$$\mathrm{CH_3CH_2CH_2CH_2CH_2CH_3} or$$ $$\mathrm{(CH_3$)_2CHCH_2CH_2CH_3}$$

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2CH_2CH_3}$$, because it is less branched and has stronger London dispersion forces.

Question 6

Rank the following compounds in order of increasing boiling point:

1. $$\mathrm{CH_3CH_2CH_2CH_3}
2$$. $$\mathrm{CH_3CH_2CH_2CH_2OH}
3$$. $$\mathrm{C_6H_{12}} ($$cyclohexane)

Accepted Answer

1 \u003c 3 \u003c 2

Question 7

Which compound is more soluble in water and why?

$$\mathrm{CH_3OCH_3} or$$ $$\mathrm{CH_3CH_2OH}$$

Accepted Answer

$$\mathrm{CH_3CH_2OH}$$, because it can form hydrogen bonds with water.

Question 8

In the reaction $$\mathrm{CH_3CH_2Cl + NH_3$ \rightarrow CH_3CH_2NH_2 + HCl}$$, which species acts as the nucleophile?

Accepted Answer

$$\mathrm{NH_3$}$$

Question 9

Which of the following best explains why alcohols generally have higher boiling points than alkanes of similar molecular weight?

Accepted Answer

Alcohols can form hydrogen bonds, which require more energy to break.

Question 10

Which of the following statements about constitutional isomers is correct?

Accepted Answer

They have the same molecular formula but different connectivity of atoms.

Question 11

Given the following p$$K_a$$ values: $$\mathrm{pK_a} of $$phenol = 10.0, $$\mathrm{pK_a} of$$ $$\mathrm{CH_3CH_2SO_3H} = -1.0$$, which is the stronger acid?

Accepted Answer

$$\mathrm{CH_3CH_2SO_3H}$$, because it has a lower p$$K_a.$$

Question 12

Which of the following best describes the movement of electrons in a nucleophilic substitution reaction?

Accepted Answer

A lone pair from the nucleophile attacks the electrophilic carbon, displacing the leaving group.

Question 13

Which of the following molecules contains both an amide and an aromatic ring functional group?

Accepted Answer

Vildagliptin

Question 14

Which of the following is NOT a constitutional isomer of $$\mathrm{C_5H_{10}}$$?

Accepted Answer

Pent-1-yne

Question 15

Which of the following best explains why $$\mathrm{CH_3CH_2OH} is $$more soluble in water than $$\mathrm{CH_3OCH_3}$$?

Accepted Answer

$$\mathrm{CH_3CH_2OH}$$ can form hydrogen bonds with water, while $$\mathrm{CH_3OCH_3}$$ cannot.

Question 16

Which of the following statements about boiling points is correct?

Accepted Answer

Branched alkanes have lower boiling points than their straight-chain isomers.

Organic Chemistry: Functional Groups, Isomerism, Bonding, and Physical Properties

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