Question 1

Which of the following statements best explains why the C–O bond in methanol ($$\ce{CH3OH}) is $$more polar than the C–H bond in methane ($$\ce{CH4}$$)?

Accepted Answer

Oxygen is more electronegative than carbon, creating a larger dipole moment in the C–O bond.

Question 2

Which of the following compounds is the strongest acid?

Accepted Answer

$$\ce{CH3COOH}$$

Question 3

Which of the following best describes the hybridization of the central carbon atom in ethene ($$\ce{C2H4}$$)?

Accepted Answer

$$\mathrm{sp^2$}$$

Question 4

A student is analyzing the IR spectrum of an unknown compound and observes a strong, broad absorption around $$3300\ \mathrm{cm}^{-1}. $$Which functional group is most likely present?

Accepted Answer

Alcohol ($$\ce{-OH})$$

Question 5

Which of the following statements about SN2 reactions is correct?

Accepted Answer

The reaction proceeds with inversion of configuration at the electrophilic carbon.

Question 6

Which of the following is the best leaving group in a nucleophilic substitution reaction?

Accepted Answer

$$\ce{H2O}$$

Question 7

Which of the following alkenes will be the major product when 2-bromobutane is treated with a strong base (e.g., $$\ce{NaOEt}) in $$ethanol?

Accepted Answer

trans-2-butene

Question 8

Which of the following statements about the E2 elimination mechanism is correct?

Accepted Answer

The reaction requires anti-coplanar geometry between the leaving group and the proton being abstracted.

Question 9

Which of the following is a meso compound?

Accepted Answer

2,3-dibromobutane

Question 10

Which of the following best explains why tertiary alcohols are more easily converted to alkyl halides with $$\ce{HCl}$$ than primary alcohols?

Accepted Answer

Tertiary alcohols form more stable carbocations during the reaction.

Question 11

Which of the following is the correct order of increasing acidity?

Accepted Answer

$$\ce{CH4} \u003c \ce{NH3} \u003c \ce{H2O} \u003c \ce{HF}$$

Question 12

Which of the following statements about Markovnikov's rule is correct?

Accepted Answer

The hydrogen atom adds to the carbon with the most hydrogens already attached.

Question 13

Which of the following is the product of the reaction of 1-butyne with excess $$\ce{HBr}$$?

Accepted Answer

2,2-dibromobutane

Question 14

Which of the following best describes the stereochemistry of the product formed when cyclohexene reacts with bromine ($$\ce{Br2}) in$$ $$\ce{CCl4}$$?

Accepted Answer

Trans-1,2-dibromocyclohexane

Question 15

Which of the following statements about the reaction coordinate diagram for an exergonic reaction is correct?

Accepted Answer

The products are at a lower energy level than the reactants.

Question 16

Which of the following is the best method to synthesize a primary alcohol from an alkene?

Accepted Answer

Hydroboration-oxidation

Question 17

Which of the following statements about the SN1 reaction mechanism is correct?

Accepted Answer

The rate-determining step is the loss of the leaving group to form a carbocation.

Question 18

Which of the following is the major product when 2-methyl-2-butene reacts with $$\ce{HBr} in $$the presence of peroxides?

Accepted Answer

1-bromo-2-methylbutane

Question 19

Which of the following best explains why $$\ce{(CH3)3COH} is $$less acidic than $$\ce{CH3OH}$$?

Accepted Answer

The tert-butyl group destabilizes the conjugate base due to electron-donating inductive effects.

Key Review Topics for Organic Chemistry II: Essential Concepts from Orgo I

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