Q: Given the IR spectrum of hex-1-yne, which absorption would you expect for the C≡C bond stretch?

Around $$2250\ \text{cm}^{-1}$$

Q: Which base would favor E2 elimination over SN2 in a reaction with a secondary alkyl halide?

Potassium tert-butoxide ($$\text{KOtBu})$$

Q: A $$1\text{H}$$ NMR spectrum shows a triplet integrating to $$3$$ protons and a quartet integrating to $$2$$ protons. What is the most likely structure?

Ethyl group ($$\text{CH}_3\text{CH}_2-)$$

Q: Which IR absorption is characteristic of a carbonyl group (C=O)?

Around $$1700\ \text{cm}^{-1}$$

Q: Which of the following is a common bulky base used in E2 reactions?

Potassium tert-butoxide ($$\text{KOtBu})$$

Question 1

Which of the following statements best describes the major contributor to a resonance hybrid?

Accepted Answer

The structure with the most delocalized electrons and minimal formal charges.

Question 2

Given the IR spectrum of hex-1-yne, which absorption would you expect for the C≡C bond stretch?

Accepted Answer

Around $$2250\ 	ext{cm}^{-1}$$

Question 3

Which functional group is indicated by a strong, broad IR absorption between $$3500$$ and $$2500\ 	ext{cm}^{-1}$$?

Accepted Answer

Carboxylic acid

Question 4

A molecule shows a $$1	ext{H}$$ NMR signal at $$7.5$$ ppm. Which region does this correspond to?

Accepted Answer

Aromatic region

Question 5

Which of the following is a poor leaving group for nucleophilic substitution?

Accepted Answer

$$	ext{OH}^-$$

Question 6

What is the product when a primary alcohol is oxidized with PCC?

Accepted Answer

Aldehyde

Question 7

Which base would favor E2 elimination over SN2 in a reaction with a secondary alkyl halide?

Accepted Answer

Potassium tert-butoxide ($$	ext{KOtBu})$$

Question 8

Which reaction mechanism is favored for a tertiary alkyl halide with a weak nucleophile?

Accepted Answer

SN1

Question 9

In the addition of HX to an alkene, which rule predicts the regioselectivity of the product?

Accepted Answer

Markovnikov's rule

Question 10

What is the expected product when a terminal alkyne is treated with $$	ext{BH}_3$$ followed by $$	ext{H}_2	ext{O}_2$$, $$	ext{OH}^-$$?

Accepted Answer

Aldehyde

Question 11

Which of the following nucleophiles is strongest for an SN2 reaction?

Accepted Answer

$$	ext{OH}^-$$

Question 12

A $$1	ext{H}$$ NMR spectrum shows a triplet integrating to $$3$$ protons and a quartet integrating to $$2$$ protons. What is the most likely structure?

Accepted Answer

Ethyl group ($$	ext{CH}_3	ext{CH}_2-)$$

Question 13

Which IR absorption is characteristic of a carbonyl group (C=O)?

Accepted Answer

Around $$1700\ 	ext{cm}^{-1}$$

Question 14

Which product is formed when a secondary alcohol is oxidized with $$	ext{K}_2	ext{Cr}_2	ext{O}_7 in$$ $$	ext{H}_2	ext{SO}_4$$?

Accepted Answer

Ketone

Question 15

Which of the following statements about SN2 reactions is correct?

Accepted Answer

SN2 reactions are favored by strong nucleophiles and primary substrates.

Question 16

What is the effect of resonance on molecular stability?

Accepted Answer

Resonance increases stability by delocalizing electrons.

Question 17

Which of the following is a common bulky base used in E2 reactions?

Accepted Answer

Potassium tert-butoxide ($$	ext{KOtBu})$$

Question 18

Which product is formed when an alkene reacts with mCPBA?

Accepted Answer

Epoxide

Question 19

What is the major product when butan-2-one undergoes oxidative cleavage?

Accepted Answer

Two carbonyl compounds

Question 20

Which mechanism is favored for a primary alkyl halide with a strong nucleophile?

Accepted Answer

SN2

Orgo 1 Review: Essential Concepts and Mechanisms

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