ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
6th Edition
ISBN: 9780072397475
Author: SMITH
Publisher: MCG
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Chapter 16, Problem 57P
Rank the aryl halides in each group in order of increasing reactivity in nucleophilic
a. chlorobenzene, p-fluoronitrobenzene, m-fluoronitrobenzene
b.
c.
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Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution: a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene c. toluene, p-cresol, benzene, p-xylene d. benzene, benzoic acid, phenol, propylbenzene e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene
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
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.
Chapter 16 Solutions
ORGANIC CHEMISTRY-STUDY GDE./SOL.MAN.
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.4 - Prob. 4PCh. 16.5 - Prob. 5PCh. 16.5 - Prob. 6PCh. 16.5 - Prob. 9PCh. 16.5 - Problem 18.9 Draw the product of each reaction
a....Ch. 16.5 - Prob. 11PCh. 16.5 - Prob. 12P
Ch. 16.5 - Prob. 13PCh. 16.6 - Prob. 14PCh. 16.6 - Problem 18.14 Draw all resonance structures for...Ch. 16.6 - Problem 18.15 Classify each substituent as...Ch. 16.7 - Prob. 17PCh. 16.9 - Prob. 22PCh. 16.10 - Problem 18.20 Draw the products of each...Ch. 16.10 - Prob. 24PCh. 16.11 - Problem 18.22 Draw the products formed when each...Ch. 16.12 - Problem 18.23 Devise a synthesis of each compound...Ch. 16.13 - Problem 18.24 Draw the products of each...Ch. 16.13 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 16.13 - Problem 18.26 Draw the products of each...Ch. 16.13 - Prob. 30PCh. 16 - Prob. 37PCh. 16 - 18.35 What is the major product formed by an...Ch. 16 - 18.36 Draw the products formed when phenol is...Ch. 16 - Problem 18.37 Draw the products formed when each...Ch. 16 - 18.38 Draw the products of each reaction.
a. d....Ch. 16 - 18.39 What products are formed when benzene is...Ch. 16 - Prob. 49PCh. 16 - 18.47 For each of the following substituted...Ch. 16 - 18.48 Consider the tetracyclic aromatic compound...Ch. 16 - 18.49 For each N-substituted benzene, predict...Ch. 16 - Prob. 54PCh. 16 - 18.51 Using resonance structures, explain why a...Ch. 16 - Prob. 56PCh. 16 - 18.53 Rank the aryl halides in each group in order...Ch. 16 - Prob. 64PCh. 16 - Prob. 65PCh. 16 - Prob. 66PCh. 16 - 18.63 Synthesize each compound from benzene and...Ch. 16 - Problem 18.64 Synthesize each compound from...
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