Question 1

Which of the following carbocations is the most stable, and why?

Accepted Answer

A tertiary allylic carbocation, because it is stabilized by both resonance and hyperconjugation.

Question 2

Which of the following compounds is aromatic according to Hückel's Rule?

Accepted Answer

Benzene ($C_6H_6$)

Question 3

Which of the following is NOT a requirement for aromaticity?

Accepted Answer

The molecule must contain only sp$^3$ hybridized atoms.

Question 4

In the Diels-Alder reaction, which product is favored under kinetic control?

Accepted Answer

The product formed fastest, usually the endo product.

Question 5

Which molecular orbital is the highest occupied molecular orbital (HOMO) in 1,3,5-hexatriene?

Accepted Answer

$\psi_3$

Question 6

Which of the following statements about SN2 reactions is TRUE?

Accepted Answer

SN2 reactions occur in a single concerted step and are favored by strong nucleophiles.

Question 7

What is the major product when 2-bromobutane reacts with a strong base such as $KOH$ in ethanol?

Accepted Answer

But-2-ene (via E2 elimination)

Question 8

Which reagent is commonly used to convert a primary alcohol ($ROH$) to a primary alkyl chloride ($RCl$)?

Accepted Answer

$SOCl_2$ in pyridine

Question 9

In the Diels-Alder reaction, which molecular orbitals interact to form the new sigma bonds?

Accepted Answer

The HOMO of the diene and the LUMO of the dienophile

Question 10

Which of the following best explains why benzene is more stable than cyclohexatriene?

Accepted Answer

Benzene is aromatic and follows Hückel's Rule ($4n+2$ pi electrons).

Question 11

Which of the following reactions will convert an alcohol to an alkyl bromide?

Accepted Answer

$ROH + HBr \rightarrow RBr$

Question 12

Which of the following is a characteristic of a thermodynamic product in a reaction?

Accepted Answer

It is the most stable product and is favored at equilibrium.

Question 13

Which of the following is true about the 1,2- and 1,4-addition of conjugated dienes?

Accepted Answer

1,2-addition is the kinetic product, while 1,4-addition is the thermodynamic product.

Question 14

Which of the following statements about E2 elimination reactions is FALSE?

Accepted Answer

E2 reactions proceed via a carbocation intermediate.

Question 15

Which of the following is the correct order of reactivity for alkyl halides in SN2 reactions?

Accepted Answer

Primary > Secondary > Tertiary

Question 16

Which of the following is NOT a method for converting an alcohol to an alkyl halide?

Accepted Answer

Reaction with $NaOH$

Question 17

Which of the following best describes the molecular orbitals in the Diels-Alder reaction?

Accepted Answer

The diene's HOMO overlaps with the dienophile's LUMO to form new bonds.

Question 18

Which of the following is a requirement for a molecule to be aromatic?

Accepted Answer

It must be planar, cyclic, and have a continuous pi system.

Question 19

Which of the following is the correct product when an alcohol reacts with $SOCl_2$ in pyridine?

Accepted Answer

An alkyl chloride ($RCl$)

Organic Chemistry Study Notes: Aromaticity, Diels-Alder Reaction, Substitution/Elimination, and Alcohol/Ether/Amines Chemistry

Study Guide - Practice Questions