Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 17, Problem 17.52SP
Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.
- a. 1-phenyl-1-bromobutane
- b. 1-phenyl-1-methoxybutane
- c. 3-phenylpropan-1-ol
- d. ethoxybenzene
- e. 1,2-dichloro-4-nitrobenzene
- f. 1-phenylpropan-2-ol
- g. p-aminobenzoic acid
- h. 2-methyl-1-phenylbutan 2-ol
- i. 5-chloro-2-methylaniline
- j. 3-nitro-4-bromobenzoic acid
- k. 3-nitro-5-bromobenzoic acid
- l. 4-butylphenol
- m. 2-(4-methylphenyl)butan-2-ol
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Students have asked these similar questions
How would you synthesize the following compounds from cyclohexanone using reagents from the table?
Use letters from the table to list reagents in the order used (first at the left).
Reagents
a
1. CH3MgBr / dry ether
2 H3O+
e
1. OsO4
i
1. BH3/THF
2. NaHSO3/H₂O
2. H₂O₂ / NaOH
b
1. C6H5 MgBr / dry ether
f
1. NaBH4
j
Mg / dry ether
2 H3O+
2. H3O+
C
PBг3
g
HOCH2CH2OH/HCI
k
H2/Pd
d
m-chloroperbenzoic
h
H3O+ / heat
1
CrO3 / H3O+
acid
a) 2-phenylcyclohexanone
b) cyclohexylbenzene
m
cyclohexanone
How would you synthesize the following compounds from cyclohexanone
using reagents from the table?
Use letters from the table to list reagents in the order used (first at the left).
Reagents
a
1. CH3MgBr/dry ether
2 H3O+
e
1. OsO4
i
1. BH3/THF
2. NaHSO3/H2O
2. H₂O₂ / NaOH
b
1. C6H5MgBr / dry ether
f
1. NaBH4
j
Mg / dry ether
2 H3O+
2. H3O+
с
PBr3
g
HOCH2CH2OH/HCI
k
H2/Pd
d
m-chloroperbenzoic
h
H3O+ / heat
I
CrO3 / H3O+
acid
m
cyclohexanone
a) cyclohexylbenzene
b) 2-phenylcyclohexanone
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3 item attempts remaining
The product of the electrophilic addition of 3-methyl-2-hexene with propanol and
bromine will produce the following major product with the following in it's name:
O a. 2-ethyl ether and 3 bromine
O b. 2-ethyl ether and 4 bromine
O c. 2-ethyl ether and 2 bromine
O d. 3-ethyl ether and pentane
O e. 3-ethyl ether and 2 bromine
Which of the following alkenes will yield 3-bromo-3-methylpentane as the major
product upon addition of HBr?
IV
Ol only
Oll and II only
OiV only
Oll only
OAII of them
Chapter 17 Solutions
Organic Chemistry (9th Edition)
Ch. 17.1 - Prob. 17.1PCh. 17.2 - Prob. 17.2PCh. 17.3 - Prob. 17.3PCh. 17.4 - Use resonance forms to show that the dipolar sigma...Ch. 17.6A - Prob. 17.5PCh. 17.6A - Prob. 17.6PCh. 17.6B - Propose a mechanism for the brommation of...Ch. 17.6B - Prob. 17.8PCh. 17.6B - Prob. 17.9PCh. 17.7 - Prob. 17.10P
Ch. 17.8 - Draw all the resonance forms of the sigma complex...Ch. 17.9 - Predict the mononitration products of the...Ch. 17.9 - Predict the mononitration products of the...Ch. 17.9 - Prob. 17.14PCh. 17.10 - Propose products (if any) and mechanisms for the...Ch. 17.10 - Predict the products (if any) of the following...Ch. 17.10 - Which reactions will produce the desired product...Ch. 17.10 - Prob. 17.19PCh. 17.11C - Prob. 17.20PCh. 17.12A - Prob. 17.21PCh. 17.12B - Propose a mechanism that shows why p-chlorotoluene...Ch. 17.12B - Propose mechanisms and show the expected products...Ch. 17.12B - Prob. 17.24PCh. 17.13A - What products would you expect from the following...Ch. 17.13A - What organocuprate reagent would you use for the...Ch. 17.13B - What products would you expect from the following...Ch. 17.13B - Prob. 17.28PCh. 17.13C - What products would you expect from the following...Ch. 17.13C - Prob. 17.30PCh. 17.14C - Prob. 17.31PCh. 17.14C - Predict the major products of the following...Ch. 17.15A - Predict the major products of treating the...Ch. 17.15B - Prob. 17.34PCh. 17.15B - Prob. 17.35PCh. 17.15B - Predict the major products when the following...Ch. 17.15C - Prob. 17.37PCh. 17.15C - a. Based on what you know about the relative...Ch. 17.15C - Show how you would synthesize the following...Ch. 17.16A - The bombardier beetle defends itself by spraying a...Ch. 17.16B - Predict the products formed when m-cresol...Ch. 17.16B - Prob. 17.42PCh. 17.16B - Prob. 17.43PCh. 17.16B - Predict the site(s) of electophilic attack on...Ch. 17.16B - Prob. 17.45PCh. 17.16B - Prob. 17.46PCh. 17.16B - Propose a synthetic sequence of this...Ch. 17.16B - Prob. 17.48PCh. 17.16B - Starting from toluene, propose a synthesis of this...Ch. 17 - Prob. 17.50SPCh. 17 - Prob. 17.51SPCh. 17 - Show how you would synthesize the following...Ch. 17 - Predict the major products of the following...Ch. 17 - Predict the major products of bromination of the...Ch. 17 - What products would you expect from the following...Ch. 17 - Prob. 17.56SPCh. 17 - Prob. 17.57SPCh. 17 - The following compound reacts with a hot,...Ch. 17 - Prob. 17.59SPCh. 17 - Electrophilic aromatic substitution usually occurs...Ch. 17 - Prob. 17.62SPCh. 17 - The most common selective herbicide for killing...Ch. 17 - Furan undergoes electrophilic aromatic...Ch. 17 - Prob. 17.65SPCh. 17 - Bisphenol A is an important component of many...Ch. 17 - Prob. 17.67SPCh. 17 - Prob. 17.68SPCh. 17 - Prob. 17.69SPCh. 17 - In Chapter14, we saw that Agent Orange contains...Ch. 17 - Phenol reacts with three equivalents of bromine in...Ch. 17 - Prob. 17.72SPCh. 17 - Prob. 17.73SPCh. 17 - A common illicit synthesis of methamphetamine...Ch. 17 - Prob. 17.75SPCh. 17 - Prob. 17.76SPCh. 17 - Prob. 17.77SPCh. 17 - Prob. 17.78SP
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