OAT Organic Chemistry Reactions Questions and Answers

Question 1

Which of the following reagents is most suitable for oxidizing a primary alcohol, such as 1-butanol, directly to a carboxylic acid, butanoic acid, in a single step?

Accepted Answer

Potassium permanganate (KMnO₄)

Answer

Pyridinium chlorochromate (PCC)

Answer

Lithium aluminum hydride (LiAlH₄)

Answer

Dess-Martin periodinane (DMP)

Question 2

In an electrophilic aromatic substitution reaction, which of the following substituents on a benzene ring would direct an incoming electrophile primarily to the meta position?

Accepted Answer

–NO₂ (Nitro)

Answer

–OH (Hydroxyl)

Answer

–CH₃ (Methyl)

Answer

–NH₂ (Amino)

Question 3

A student treats acetone (propanone) with methylmagnesium bromide (CH₃MgBr), followed by an acidic workup with H₃O⁺. What is the major organic product of this reaction sequence?

Accepted Answer

tert-Butanol (2-methyl-2-propanol)

Answer

2-Propanol

Answer

2-Butanone

Answer

1-Propanol

Question 4

The reaction of (2E,4E)-hexa-2,4-diene with maleic anhydride is a classic example of which type of reaction?

Accepted Answer

Diels-Alder Cycloaddition

Answer

SN2 Nucleophilic Substitution

Answer

E2 Elimination

Answer

Aldol Condensation

Question 5

When 2-bromopropane is treated with sodium ethoxide (NaOEt) in ethanol, two products are formed via competing reaction pathways. Which statement best describes the expected outcome?

Accepted Answer

The SN2 product, 2-ethoxypropane, and the E2 product, propene, will both be formed.

Answer

The SN1 product, 2-ethoxypropane, will be the exclusive product.

Answer

The E1 product, propene, will be the major product due to the weak base.

Answer

The reaction will not proceed as 2-bromopropane is an unreactive substrate.

Question 6

Which of the following molecules could undergo a self-aldol condensation reaction in the presence of a dilute base?

Accepted Answer

Acetaldehyde (ethanal)

Answer

Formaldehyde (methanal)

Answer

Benzaldehyde

Answer

2,2-Dimethylpropanal