Question 1

Which of the following statements best explains why tertiary alkyl halides generally undergo $$S_N1$$ reactions more readily than primary alkyl halides?

Accepted Answer

Tertiary alkyl halides form more stable carbocations due to hyperconjugation and inductive effects.

Question 2

A student is analyzing the IR spectrum of an unknown compound and observes a strong, broad absorption around $$3300\ \mathrm{cm}^{-1}. $$Which functional group is most likely present?

Accepted Answer

Alcohol

Question 3

Which of the following is the correct order of increasing acidity for the following compounds: ethanol, phenol, and acetic acid?

Accepted Answer

Ethanol \u003c Phenol \u003c Acetic acid

Question 4

Which of the following best describes the product(s) of the acid-catalyzed hydration of 2-methylpropene ($$\mathrm{CH_2$=C(CH_3$)_2}$$)?

Accepted Answer

2-methyl-2-propanol as the major product, via Markovnikov addition

Question 5

A compound with the molecular formula $$C_4H_{10}O is $$treated with concentrated $$H_2SO_4$$ and heat. Which of the following is the most likely major product?

Accepted Answer

An alkene formed by E1 elimination

Question 6

Which of the following statements about the $$E2$$ elimination mechanism is correct?

Accepted Answer

The $$E2$$ mechanism requires a strong base and anti-coplanar geometry between the leaving group and the hydrogen being abstracted.

Question 7

Which of the following best explains why tosylates ($$\mathrm{ROTs}) $$are good leaving groups in nucleophilic substitution reactions?

Accepted Answer

Tosylates stabilize the negative charge by resonance delocalization over the sulfonyl group.

Question 8

A student is asked to assign the $$(R) or$$ $$(S)$$ configuration to the following chiral center: $$\mathrm{CH_3CH(OH)CH_2Br}. $$Which of the following is the correct configuration for the chiral carbon (the one bonded to OH)?

Accepted Answer

$$(S)$$

Question 9

Which of the following best describes the product of the reaction of 1-butene with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$}$$?

Accepted Answer

1,2-dibromobutane

Question 10

Which of the following statements about the $$S_N2$$ reaction mechanism is correct?

Accepted Answer

The $$S_N2$$ mechanism is favored by strong nucleophiles and less hindered (primary) substrates.

Question 11

Which of the following best explains why cyclohexane adopts a chair conformation?

Accepted Answer

To minimize both torsional and angle strain, resulting in a more stable structure.

Question 12

A compound is found to have two stereocenters and is superimposable on its mirror image. Which of the following best describes this compound?

Accepted Answer

It is a meso compound.

Question 13

Which of the following is the best description of the product formed when 1-butyne reacts with $$\mathrm{H_2$} in $$the presence of Lindlar's catalyst?

Accepted Answer

cis-2-butene

Question 14

Which of the following statements about the Markovnikov rule is correct?

Accepted Answer

In the addition of $$\mathrm{HX} to an $$alkene, the hydrogen atom adds to the carbon with the greatest number of hydrogens.

Question 15

Which of the following best describes the product of the acid-catalyzed dehydration of 2-butanol?

Accepted Answer

2-butene as the major product

Question 16

A student is given the $$^1H $$NMR spectrum of ethyl acetate. Which of the following best describes the expected splitting pattern for the methyl group attached to the oxygen ($$\mathrm{OCH_2CH_3}$$)?

Accepted Answer

A triplet

Question 17

Which of the following is the correct product of the Williamson ether synthesis between sodium ethoxide ($$\mathrm{NaOEt}) $$and 1-bromopropane?

Accepted Answer

Ethyl propyl ether

Question 18

Which of the following best explains why $$E2$$ eliminations of cyclohexyl halides occur only when the leaving group and the hydrogen to be abstracted are both axial?

Accepted Answer

The anti-coplanar geometry required for $$E2$$ elimination is only possible when both groups are axial.

Question 19

Which of the following best describes the product of the base-catalyzed epoxide ring opening of ethylene oxide with methanol ($$\mathrm{CH_3OH}$$)?

Accepted Answer

1-methoxyethanol

Organic Chemistry I: Core Concepts, Mechanisms, and Applications – Study Guide

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