Question 1

Which of the following is a correct definition of a Lewis base?

Accepted Answer

A species that donates an electron pair

Question 2

Which of the following organic compounds, when ionized, would have the weakest conjugate base?

Accepted Answer

$$\mathrm{CH}_4$$, pK$$_a = 52$$

Question 3

Which species is a carbon-based Lewis acid?

Accepted Answer

$$\mathrm{CH}_3^+$$

Question 4

Which of the following molecules or ions has a nitrogen with a formal charge of -1?

Accepted Answer

III

Question 5

What is the formal charge on the oxygen atom in the following structure? $$\mathrm{O}$$ with three lone pairs and a single bond to $$\mathrm{H}.$$

Accepted Answer

-1

Question 6

What is the hybridization of the arrow-indicated atom in $$\mathrm{HC\equiv CH}$$?

Accepted Answer

$$sp$$

Question 7

Which of the following molecules would be water soluble?

Accepted Answer

I

Question 8

Which compound listed below is a secondary alcohol?

Accepted Answer

II: $$\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}(\mathrm{OH})\mathrm{CH}_3$$

Question 9

Which functional groups are present in the molecule of capsaicin?

Accepted Answer

Alkene, ketone, alcohol, ether

Question 10

In the following reaction, which reactant is behaving as the Lewis Acid (LA) and which reactant is behaving as the Lewis Base (LB)? $$\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{Cl} + \mathrm{Na}^+\mathrm{CN}^- \rightarrow \mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{CN} + \mathrm{NaCl}$$

Accepted Answer

Reactant 1: LA, Reactant 2: LB

Question 11

Which of the following schemes correctly shows the electron flow for the nucleophilic substitution reaction between $$\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{Cl}$$ and $$\mathrm{Na}^+\mathrm{CN}^-$$?

Accepted Answer

Scheme 2

Question 12

Which of the following is NOT a resonance form of the anionic species in the box (benzylic anion)?

Accepted Answer

I and III

Question 13

Which of the following species is a resonance form of the species in the box (phenoxide anion)?

Accepted Answer

II

Question 14

Which compound listed below is a tertiary amine?

Accepted Answer

III

Question 15

What alkyl group is attached to the oxygen in the following ester: $$\mathrm{CH}_3\mathrm{CH}_2\mathrm{COOCH(CH_3$)_2}$$?

Accepted Answer

Isopropyl

Question 16

Which compound would you expect to have the highest boiling point?

Accepted Answer

$$\mathrm{HOCH}_2\mathrm{CH}_2\mathrm{CH}_2\mathrm{OH}$$

Question 17

Which of the following molecules is a secondary alcohol?

Accepted Answer

III

Question 18

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

Accepted Answer

V

Question 19

Which of the following compounds contains both a primary alcohol and an alkene functional group?

Accepted Answer

Alkene, 1° alcohol, aldehyde

Organic Chemistry: Fundamental Concepts and Practice Questions

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