Question 1

Which of the following best describes an electrophilic addition reaction to an alkene?

Accepted Answer

A reaction in which one $$\pi$$ bond is broken and two new $$\sigma$$ bonds are formed.

Question 2

Markovnikov’s Rule predicts the regiochemistry of electrophilic addition to alkenes. According to this rule, where does the electrophile add?

Accepted Answer

To the carbon of the double bond with the greater number of hydrogens.

Question 3

In the hydrohalogenation of 2-methylpropene with HBr, what is the major product?

Accepted Answer

2-bromo-2-methylpropane

Question 4

Which intermediate is formed during the acid-catalyzed hydration of an alkene?

Accepted Answer

A carbocation

Question 5

What is the product of the reaction of 1-methylcyclohexene with $$\mathrm{Hg(OAc)_2}$$, $$\mathrm{H_2O}$$ followed by $$\mathrm{$$NaBH_4$$}$$, $$\mathrm{NaOH}$$?

Accepted Answer

Trans-1-methylcyclohexanol

Question 6

Which of the following statements about hydroboration-oxidation of alkenes is correct?

Accepted Answer

It results in anti-Markovnikov addition of water across the double bond.

Question 7

During the halogenation of an alkene (e.g., with $$\mathrm{Br_2$}$$), what is the key intermediate?

Accepted Answer

A bromonium ion

Question 8

Which of the following best describes the product of ozonolysis of 1-butene followed by reductive workup with $$\mathrm{Zn/HOAc}$$?

Accepted Answer

Propanal and formaldehyde

Question 9

What is the stereochemical outcome of syn addition in the hydrogenation of an alkene using $$\mathrm{H_2$}$$ and a metal catalyst?

Accepted Answer

Both hydrogens add to the same face of the double bond.

Question 10

Which of the following reagents is commonly used for the epoxidation of alkenes?

Accepted Answer

A peroxy acid such as $$\mathrm{mCPBA}$$

Question 11

In the presence of peroxides, the addition of HBr to an alkene proceeds via which mechanism?

Accepted Answer

A free radical mechanism resulting in anti-Markovnikov addition

Question 12

Which of the following is a product of the oxidative cleavage of 1,2-dimethylcyclohexene with hot $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

A ketone and a carboxylic acid

Question 13

What is the major product when cyclohexene reacts with $$\mathrm{Br_2$} in $$water?

Accepted Answer

Trans-2-bromocyclohexanol

Question 14

Which of the following best describes the propagation step in free radical polymerization?

Accepted Answer

A radical adds to a monomer, generating a new radical.

Question 15

Which of the following is true about the hydration of alkenes using acid catalysis?

Accepted Answer

The reaction proceeds via a carbocation intermediate and follows Markovnikov's rule.

Question 16

Which of the following is a correct statement about the stereochemistry of halohydrin formation from alkenes?

Accepted Answer

The halogen and hydroxyl groups add to opposite faces (anti addition).

Question 17

Which of the following is a product of the ozonolysis of 2-methyl-2-butene followed by oxidative workup with $$\mathrm{H_2O_2}$$?

Accepted Answer

Acetone and acetic acid

Question 18

Which of the following best explains why hydroboration-oxidation gives anti-Markovnikov alcohols?

Accepted Answer

Boron adds to the less substituted carbon due to steric and electronic effects.

Question 19

Which of the following is a correct statement about the mechanism of oxymercuration-demercuration?

Accepted Answer

It avoids carbocation rearrangements by forming a mercurinium ion intermediate.

Step-by-Step Guidance for Electrophilic Addition Reactions in Organic Chemistry

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