Question 1

Which of the following resonance forms of cyclopentadienyl cation is the most stable, and why?

Accepted Answer

The form where the positive charge is on a carbon atom that is part of the aromatic system, because aromaticity stabilizes the charge.

Question 2

Which of the following Lewis structures for $\mathrm{CH_3CH_2CHNH_2}$ is valid?

Accepted Answer

A structure where nitrogen has three bonds and one lone pair, and all atoms obey the octet rule.

Question 3

Tamiflu contains several functional groups. Which of the following is NOT present in Tamiflu?

Accepted Answer

Ketone

Question 4

Which of the following compounds can exhibit cis-trans isomerism?

Accepted Answer

$\mathrm{CH_3CH=CHCH_3}$

Question 5

In the structure of kainic acid, which atoms are sp$^2$ hybridized?

Accepted Answer

All carbons in the aromatic ring and any carbonyl carbon.

Question 6

For the bond between two carbon atoms in ethylene ($\mathrm{C_2H_4}$), how many sigma and pi bonds are present?

Accepted Answer

1 sigma bond and 1 pi bond

Question 7

In the acid-base reaction between acetic acid and ammonia, which direction does the equilibrium favor?

Accepted Answer

Formation of the weaker acid and weaker base

Question 8

Rank the following bases in order of decreasing basicity: $\mathrm{NH_2^-}$, $\mathrm{OH^-}$, $\mathrm{CH_3COO^-}$.

Accepted Answer

$\mathrm{NH_2^-} > \mathrm{OH^-} > \mathrm{CH_3COO^-}$

Question 9

Given the name 1-chloro-3-propyl-1,2-dimethylpentane, what is the correct IUPAC name for the compound?

Accepted Answer

3-chloro-3,5-dimethylheptane

Question 10

In the structure of vanillin, which functional group is responsible for its characteristic aroma?

Accepted Answer

Aldehyde

Question 11

Which of the following Newman projections represents the lowest energy conformation for 1,2-dibromoethane?

Accepted Answer

Staggered conformation with Br atoms anti to each other

Question 12

Which of the following statements about resonance structures is correct?

Accepted Answer

The true structure is a hybrid of all valid resonance forms.

Question 13

Which of the following molecules violates the octet rule?

Accepted Answer

A carbon atom with five bonds

Question 14

Which orbital interaction forms a pi bond?

Accepted Answer

$\mathrm{p}$-$\mathrm{p}$ sideways overlap

Question 15

Which of the following is the correct Lewis structure for ammonia ($\mathrm{NH_3}$)?

Accepted Answer

Nitrogen with three single bonds to hydrogen and one lone pair

Question 16

Which of the following is a correct statement about acid-base equilibrium?

Accepted Answer

Equilibrium favors formation of the weaker acid and weaker base.

Question 17

Which of the following is NOT a valid functional group found in Tamiflu?

Accepted Answer

Alcohol

Question 18

Which of the following molecules can NOT exhibit cis-trans isomerism?

Accepted Answer

$\mathrm{CH_2=CH_2}$

Question 19

Which of the following is the correct IUPAC name for the compound with the structure: a seven-carbon chain with methyl groups at positions 3 and 5, and a chlorine at position 3?

Accepted Answer

3-chloro-3,5-dimethylheptane

Organic Chemistry I: Practice Exam 1 Study Notes

Study Guide - Practice Questions

Study Guide - Flashcards