The molecule must have 4n $$\\pi$$ electrons.

Question 1

Which of the following statements correctly describes the product of an epoxide ring opening under acidic conditions?

Accepted Answer

The nucleophile attacks the more substituted carbon, and the oxygen becomes an alcohol.

Question 2

In the 1,2 vs 1,4 addition to conjugated dienes, which product is favored at low temperature and why?

Accepted Answer

1,2 product is favored because it is the kinetic product.

Question 3

Which of the following is the correct IUPAC name for the compound CH$$_2=CH-CH=CH$_2$$?

Accepted Answer

1,3-butadiene

Question 4

A student reacts R-SH with [O]. What is the major product?

Accepted Answer

R-S-S-R (disulfide)

Question 5

Which of the following best describes aromaticity according to Huckel's Rule?

Accepted Answer

A molecule must be cyclic, flat, conjugated, and have 4n+2 $$\pi$$ electrons.

Question 6

Which of the following is the correct product when an epoxide is opened with HBr?

Accepted Answer

Br attaches to the more substituted carbon, OH to the less substituted carbon.

Question 7

Which of the following is the correct name for the compound CH$$_3-C$_6H$_4-Br$$, where the methyl and bromine are on adjacent carbons?

Accepted Answer

o-bromotoluene

Question 8

Which statement about conjugation stability is correct?

Accepted Answer

Conjugated systems are more stable than cumulated systems.

Question 9

A compound with the structure CH$$_2=CH-CH=CH-CH$_2-CH$_3 is $$named:

Accepted Answer

1,3-hexadiene

Question 10

Which of the following is true about the acidity of phenol, cyclopentadiene, and benzene?

Accepted Answer

Phenol is more acidic than cyclopentadiene and benzene.

Question 11

When drawing the Diels-Alder reaction, which product is favored if the substituents are endo and exo?

Accepted Answer

Endo product is favored due to secondary orbital interactions.

Question 12

Which of the following is the correct parent name for a molecule with a triangle containing an oxygen atom?

Accepted Answer

Epoxy

Question 13

Which of the following is the correct product when an epoxide is opened with HOH (water) under basic conditions?

Accepted Answer

HO attaches to the less substituted carbon, OH to the less substituted carbon (trans-diol).

Question 14

Which of the following is NOT a requirement for aromaticity?

Accepted Answer

The molecule must have 4n $$\pi$$ electrons.

Question 15

Which of the following is the correct product when R-SH is reacted with R-SH?

Accepted Answer

R-S-S-R (disulfide)

Question 16

Which of the following statements about Diels-Alder reactions is correct?

Accepted Answer

Electron-withdrawing groups on the dienophile favor the reaction.

Question 17

Which of the following is the correct name for CH$$_3CH$_2CH$_2SH$$?

Accepted Answer

1-propanethiol

Question 18

Which of the following is true about the attack of a nucleophile on an epoxide under basic conditions?

Accepted Answer

The nucleophile attacks the less substituted carbon.

Question 19

Which of the following is the correct product when R-S-R is oxidized?

Accepted Answer

R-SO$$_2-R ($$sulfonide)

Question 20

Which of the following is the correct shortcut memory for the 1,2 vs 1,4 addition in conjugated dienes?

Accepted Answer

1,2 is fast, 1,4 is stable.

Organic Chemistry Mechanisms, Reactions, and Nomenclature: Exam Master Guide

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