1. Which of the following descriptions best matches the sequence of events that

Question

1. Which of the following descriptions best matches the sequence of events that occurs in the reaction below

a)an H abstraction by a base, followed by an intramolecular SN2

b)an intramolecular SN2, followed by an H abstraction by a base

c)formation of a carbocation by ionizing the C-Br bond, followed intramolcular SN1, followed by an H abstraction by a base

d)formation of a carbocation by ionizing the C-Br bond, followed by H abstraction by a base leading to elimination

e) none of the above

2.Which of the methods below is not effective at synthesizing tert-butyl methyl ether?

a) (CH3)3C?O?Na? + CH3Br ?

b)(CH3)3C?Br + CH3O?Na? ?

c)H2C=C(CH3)2 + CH3OH (acid catalyzed) ?

d) (CH3)3C?Br + CH3OH (?) ?

3.What is the correct IUPAC name of the following compound?

a)4-isopropyl-3-methyl-2-butanol

b)2,3,4-trimethyl-4-pentanol

c)1,1,2,3-tetramethyl-4-pentanol

d)3,4,5-trimethyl-2-hexanol

e)3,4,5,5-tetramethyl-2-pentanol

4.What would happen if the compound below were to undergo Friedel-Crafts acylation?

a)Substitution would occur in ring B, para to the CH2 group

b) Substitution would occur in ring A, ortho to the nitro group

c) Substitution would occur in ring B, meta to the CH2 group

d) Substitution would occur in ring A, ortho to the CH2 group

e) no reaction would take place because both rings are deactivated

5.Which of the following best describe the compound below?

a) the compound would be aromatic if planar

b) the compound would be nonaromatic if planar

c) the compound would be antiaromatic if planar

d) the compound would be aromatic if nonplanar

e) the compound would be antiaromatic if nonplan

Explanation / Answer

1. b)an intramolecular SN2, followed by an H abstraction by a base 2. a) (CH3)3C—O-Na+ + CH3Br 3. e)3,4,5,5-tetramethyl-2-pentanol 4. a)Substitution would occur in ring B, para to the CH2 group 5. a) the compound would be aromatic if planar

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