Question 1

Which of the following compounds would show the most downfield (leftmost) single peak in its $$^1H $$NMR spectrum?

Accepted Answer

Benzene

Question 2

Which of the following statements best explains why para-nitrotoluene is less acidic than ortho-nitrotoluene?

Accepted Answer

The para isomer has less resonance stabilization of the conjugate base.

Question 3

Which of the following is the correct IUPAC name for the compound with the structure $$\mathrm{CH_2$=CHCH_2CH_2OH}$$?

Accepted Answer

But-3-en-1-ol

Question 4

Which of the following reagents is best used to selectively reduce an ester to an aldehyde?

Accepted Answer

DIBAL-H

Question 5

Which of the following is a correct structure for ethyl acetoacetate?

Accepted Answer

$$\mathrm{CH_3COCH_2COOEt}$$

Question 6

Which of the following is a true statement about the acidity of 1-naphthol versus 2-naphthol?

Accepted Answer

2-Naphthol is more acidic due to better resonance stabilization of its conjugate base.

Question 7

Which of the following cyclic compounds is aromatic?

Accepted Answer

Cyclopentadienyl anion

Question 8

Which of the following best describes the role of MCPBA in organic synthesis?

Accepted Answer

Oxidizing agent used for epoxidation of alkenes

Question 9

A student attempts to reduce a carboxylic acid to a primary alcohol. Which reagent should they use?

Accepted Answer

LAH (Lithium aluminum hydride)

Question 10

Which of the following best explains why chromic acid is not suitable for the selective oxidation of a primary alcohol to an aldehyde?

Accepted Answer

Chromic acid is too strong and oxidizes primary alcohols all the way to carboxylic acids.

Question 11

Which of the following is the correct mechanism for the formation of an imine from a ketone and a primary amine?

Accepted Answer

Nucleophilic addition of the amine to the carbonyl, followed by dehydration

Question 12

Which of the following best describes the function of LDA (lithium diisopropylamide) in organic synthesis?

Accepted Answer

Strong, non-nucleophilic base used to generate enolates

Question 13

A student is asked to synthesize 3-methylbut-3-enal. Which of the following is the correct structure?

Accepted Answer

$$\mathrm{CH_2$=C(CH_3$)CH=O}$$

Question 14

Which of the following best explains why a reaction requires more than one equivalent of base in an aldol condensation?

Accepted Answer

Base is consumed in both enolate formation and in the final elimination step.

Question 15

Which of the following is the correct product of the reaction of ethyl acetoacetate with LDA followed by methyl iodide?

Accepted Answer

Alkylation at the alpha position to give $$\mathrm{CH_3COCH(Me)COOEt}$$

Question 16

Which of the following is a correct statement about the aromaticity of cyclopentadienyl anion?

Accepted Answer

It is aromatic because it has 6 $$\pi$$ electrons and a planar, fully conjugated ring.

Question 17

Which of the following is the correct structure for indole?

Accepted Answer

A bicyclic structure with a benzene ring fused to a five-membered nitrogen-containing ring

Question 18

Which of the following best describes the product of the reaction of a ketone with MCPBA?

Accepted Answer

An ester via Baeyer-Villiger oxidation

Question 19

Which of the following is the correct order of chemical shift (from most downfield to most upfield) for the following protons: aromatic, alkene, alkane, aldehyde?

Accepted Answer

Aldehyde \u003e aromatic \u003e alkene \u003e alkane

CHEM 224 Organic Chemistry II Final Exam Study Guidance

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