Question 1

Which of the following statements best describes the geometry and bond rotation of a molecule with a carbon-carbon double bond?

Accepted Answer

The geometry is trigonal planar and rotation around the double bond is restricted due to the presence of a $$\pi$$ bond.

Question 2

Given the following pKa values: acetic acid ($$pK_a = 4.8$$), phenol ($$pK_a = 10.0$$), and ethanol ($$pK_a = 16.0$$), which compound is the strongest acid and why?

Accepted Answer

Acetic acid, because it has the lowest pKa and thus is most likely to lose a proton.

Question 3

Which of the following best explains why the conjugate base of trifluoroacetic acid ($$CF_3COOH) is $$more stable than that of acetic acid ($$CH_3COOH$$)?

Accepted Answer

The trifluoromethyl group is electron-withdrawing, stabilizing the negative charge via induction.

Question 4

Which of the following is the correct IUPAC name for the compound with the structure $$CH_3CH_2CH_2CH_2OH$$?

Accepted Answer

1-Butanol

Question 5

Which of the following statements about resonance is TRUE?

Accepted Answer

Resonance delocalizes electrons, stabilizing the molecule.

Question 6

A molecule has the following structure: $$CH_3CH_2CH_2Br. $$What is the correct IUPAC name?

Accepted Answer

1-Bromopropane

Question 7

Which of the following best describes the difference between conformational and configurational isomers?

Accepted Answer

Conformational isomers differ by rotation around single bonds, while configurational isomers require breaking covalent bonds to interconvert.

Question 8

Which of the following cyclohexane chair conformations is the most stable for methylcyclohexane?

Accepted Answer

The conformation with the methyl group in the equatorial position.

Question 9

Which of the following molecules is chiral?

Accepted Answer

$$CH_3CHBrCHFCH_3$$

Question 10

Which of the following statements about Newman projections is correct?

Accepted Answer

The staggered conformation is the lowest energy conformation due to minimized torsional strain.

Question 11

Which of the following best describes a meso compound?

Accepted Answer

A compound with chiral centers and a plane of symmetry, making it achiral.

Question 12

Which of the following is the correct order of increasing boiling point for the following compounds: methane, ethanol, and ethanoic acid?

Accepted Answer

Methane \u003c Ethanol \u003c Ethanoic acid

Question 13

Which of the following is the correct curved arrow notation for the deprotonation of acetic acid by hydroxide ion?

Accepted Answer

Arrow from the O-H bond of acetic acid to the oxygen atom, and arrow from hydroxide's lone pair to the hydrogen of acetic acid.

Question 14

Which of the following best describes the hybridization of the central carbon atom in ethyne ($$C_2H_2$$)?

Accepted Answer

$$sp$$

Question 15

Which of the following statements about the effect of resonance on acidity is correct?

Accepted Answer

Resonance stabilization of the conjugate base increases the acidity of the acid.

Question 16

Which of the following is the correct IUPAC name for the compound shown below?

A cyclohexane ring with a methyl group at carbon 1 and a bromine at carbon 3 (cis to each other).

Accepted Answer

cis-1-Bromo-3-methylcyclohexane

Question 17

Which of the following best describes the relationship between (R)-2-butanol and (S)-2-butanol?

Accepted Answer

They are enantiomers.

Question 18

Which of the following is the correct description of the E/Z system for alkenes?

Accepted Answer

E isomers have higher priority groups on opposite sides, Z isomers have them on the same side.

Question 19

Which of the following best explains why $$NH_3 is a $$base according to the Brønsted-Lowry definition?

Accepted Answer

$$NH_3$$ accepts a proton.

Question 20

Which of the following statements about the solubility of alcohols in water is correct?

Accepted Answer

Alcohols are soluble in water because they can form hydrogen bonds with water molecules.

Organic Chemistry Study Guide: Foundations, Acids/Bases, Nomenclature, and Stereochemistry

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