Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 16, Problem 57P

Rank the aryl halides in each group in order of increasing reactivity in nucleophilic aromatic substitution by an addition–elimination mechanism.

a. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene

b. 1 -fluoro- 2 , 4 -dinitrobenzene, 1 -fluoro- 3 , 5 -dinitrobenzene, 1 -fluoro- 3 , 4 -dinitrobenzene

c. 1 -fluoro- 2 , 4 -dinitrobenzene, 4 -chloro- 3 -nitrotoluene, 4 -fluoro- 3 -nitrotoluene

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d. 12. What is the simplest fused aromatic hydrocarbon? a. Naphthalene b. 1,2-Benzylpyrene c. Methylbenzene d. Cyclobenzene 13. In electrophilic aromatic substitution reactions, a phenyl substituent on the aromatic ring is a. a deactivator and a m-director b. a deactivator and an o,p-director c. an activator and an o,p-director d. none of the above 14. Acetylide ion formation requires a strong base like NaNH2 which in turn is made using ammonia and Na. The catalyst used in this reaction is a. Cu b. Fe C. Pt d. Pd 15. Hydroboration-Oxidation of terminal alkyne results in the formation of an a. Aldehyde by Markovnikov mechanism b. Ketone by anti-Markovnikov mechanism c. Enol by Markovnikov mechanism d. Aldehyde by anti-Markovnikov mechanism 16.p-Methoxybenzaldehyde can be prepared from anisole using the Gatterman- Koch formylation. What mixture of reagents is necessary for this process? a. CO, HCI, AICI3, CuCI b. CO, SO3, H2SO4 CO2, HCI, AICI3 d. CO2, SO3, H2SO4 e. CO2, HNO3, H2SO4 C.
What is the first step in the general mechanism for electrophilic aromatic substitution? a. aromatic ring protonation b.loss of the electrophilic aromatic ring c. deprotonation of the aromatic ring d.addition of the electrophilic to the aromatic ring.
Synthesize each compound from benzene and any other organic or inorganic reagents. NH2 NO2 Br. a. е. NH2 Br CH3 Br NH2 b. d. HOOC NO2 (РАВA) sunscreen component

Chapter 16 Solutions

Organic Chemistry (6th Edition)

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