Question 1

Which of the following statements best describes the acidic cleavage of an epoxide containing a secondary carbon?

Accepted Answer

The nucleophile attacks the more substituted carbon because it is more stabilized by carbocation character.

Question 2

Which reagent would you use to synthesize a thiol from an alkyl halide?

Accepted Answer

NaSH

Question 3

Which of the following compounds is conjugated?

Accepted Answer

CH$$_2=CH-CH=CH$_2$$

Question 4

Arrange the following compounds in order of increasing conjugation: 1) CH$$_2=CH-CH$_2-CH$_3$$, 2) CH$$_2=CH-CH=CH$_2$$, 3) Benzene.

Accepted Answer

1 \u003c 2 \u003c 3

Question 5

What is the major product when 1,3-butadiene reacts with HBr at low temperature?

Accepted Answer

1,2-addition product: CH$$_2=CH-$$CHBr-CH$$_3$$

Question 6

Which diene is best suited for a Diels-Alder reaction?

Accepted Answer

cis-1,3-butadiene

Question 7

Which dienophile will react fastest in a Diels-Alder reaction?

Accepted Answer

Maleic anhydride

Question 8

What is the endo product in a Diels-Alder reaction?

Accepted Answer

The product where the electron-withdrawing group is oriented towards the diene's double bonds.

Question 9

Which of the following is aromatic according to Hückel's rule?

Accepted Answer

Benzene

Question 10

Which of the following ions is aromatic?

Accepted Answer

Cyclopentadienyl anion ($$C_5H_5^-)$$

Question 11

Which of the following compounds is anti-aromatic?

Accepted Answer

Cyclobutadiene

Question 12

Why is the acidity of phenol greater than that of cyclohexanol?

Accepted Answer

Phenol is aromatic and its conjugate base is stabilized by resonance.

Question 13

What is the correct IUPAC name for a benzene ring with a methyl group at position 1 and a nitro group at position 3?

Accepted Answer

m-nitrotoluene

Question 14

Which of the following is a heterocyclic aromatic compound?

Accepted Answer

Pyridine

Question 15

Which of the following best describes the basic cleavage of an epoxide?

Accepted Answer

The nucleophile attacks the less substituted carbon due to less steric hindrance.

Question 16

Which of the following is the correct product when 1,3-butadiene reacts with Br$$_2 at $$high temperature?

Accepted Answer

1,4-dibromo-2-butene

Question 17

Which of the following is NOT a requirement for aromaticity?

Accepted Answer

The molecule must have 4n $$	ext{π}$$ electrons.

Question 18

Which of the following is the correct IUPAC name for a benzene ring with two chlorine atoms at positions 1 and 4?

Accepted Answer

1,4-dichlorobenzene

Question 19

Which of the following is a correct statement about the Diels-Alder reaction with a (Z)-dienophile?

Accepted Answer

The product will have substituents on the same side of the newly formed ring.

Organic Chemistry Exam 2 Study Guide: Epoxides, Conjugation, Aromaticity, and Related Reactions

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