Question 1

Which of the following best describes the hybridization of the nitrogen atom in the amide group of aspartame?

Accepted Answer

$$sp^2$$

Question 2

In the Tylenol (acetaminophen) molecule, how many $$	ext{o-bonds}$$ and $$	ext{π-bonds}$$ are present?

Accepted Answer

$$13$$ 	ext{ o-bonds},
$$4$$ 	ext{ π-bonds}$

Question 3

Which of the following molecules contains both an ester and an amine functional group?

Accepted Answer

Aspartame

Question 4

Given the following orbital interaction: $$2p_x$$ and $$2p_x$$ side-by-side overlap, what type of bond is formed?

Accepted Answer

$$	ext{π-bond}$$

Question 5

Which of the following acids is the strongest?

Accepted Answer

HCl

Question 6

What is the formal charge on the oxygen atom in the following structure: $$\mathrm{CH_3CH_2O^-}$$?

Accepted Answer

$$-1$$

Question 7

Which of the following molecules will have the highest boiling point?

Accepted Answer

1-butanol

Question 8

What is the molecular formula for the following molecule: a benzene ring attached to a pyridine ring and a vinyl group?

Accepted Answer

$$C_{11}H_9N$

Question 9

Which resonance structure is more stable for the acetate ion ($$\mathrm{CH_3COO^-}$$)?

Accepted Answer

The structure with the negative charge delocalized over both oxygens

Question 10

Why is the pKa of the C-H proton in acetylene ($$\mathrm{HC\equiv CH}) $$much lower than that of ethane ($$\mathrm{CH_3CH_3}$$)?

Accepted Answer

The conjugate base of acetylene is stabilized by $$sp$$ hybridization, which holds the negative charge closer to the nucleus.

Question 11

Which of the following is the correct mechanism for the acid-base reaction between acetic acid and sodium hydroxide?

Accepted Answer

Deprotonation of acetic acid by hydroxide to form acetate and water

Question 12

Which of the following molecules contains a tertiary amine?

Accepted Answer

N,N-dimethylethylamine

Question 13

What is the IUPAC name for the following structure: a seven-carbon chain with ethyl groups at C-3 and methyl groups at C-2 and C-6?

Accepted Answer

3-ethyl-2,6-dimethylheptane

Question 14

Which of the following statements about resonance structures is TRUE?

Accepted Answer

The most stable resonance structure has the negative charge on the most electronegative atom.

Question 15

Which of the following molecules is aromatic?

Accepted Answer

Benzene

Question 16

Which of the following is the correct pKa value for a carboxylic acid?

Accepted Answer

$$4$$

Question 17

Which of the following best explains why fluorine substitution increases the acidity of ethanol?

Accepted Answer

Fluorine is highly electronegative and stabilizes the negative charge on the conjugate base via inductive effect.

Question 18

Which of the following is NOT a functional group present in aspartame?

Accepted Answer

Aldehyde

Question 19

Which of the following molecules will have the lowest boiling point?

Accepted Answer

Butane

Question 20

Which of the following best describes the orbital interaction in a $$	ext{σ-bond}$$ between two hydrogen atoms?

Accepted Answer

Head-on overlap of two $$1s$$ orbitals

Organic Chemistry I: Key Concepts and Practice for Exam 1

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