18.14: Solutions to Additional Exercises
- Page ID
- 158601
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18-2
18-3 This is just one possible way to synthesize it.
18-4 The bromine should be in the meta position. Right now it is in the ortho position, from perhaps having the ethyl group present first and then the having it substituted there. BUT the ethyl group is last to form, and the aldehyde and nitro groups would both encourage a meta substitution.
18-5 Answer: A
18-6
18-7
18-8
18-9 1-chloro-2-methylbenzene and 1-chloro-4-methylbenzene
18-10
18-11
Halogenation, Nitration, and Sulfonation of Benzene
18-12:
18-13:
18-14:
Answer: A
Activating, Ortho-, Para-Directing Substituents
18-15:
18-16:
18-17:
Deactivating, Meta-Directing Substituents
18-18:
18-19:
18-20:
Answer: B
Halogen Substitutes: Deactivating, but Ortho, Para-Directing
18-21:
Answer: B
18-22:
18-23:
Effects of Multiple Substituents on Electrophilic Aromatic Substitution
18-24:
18-25:
18-26:
Friedel-Crafts Alkylation/Acylation
18-27:
18-28:
Friedel-Crafts alkylation using 1-chloropropane is not the best way to synthesize propylbenzene. You will end up with (propan-2-yl)benzene as your main product due to a hydride shift occurring during an intermediate step. A better route of synthesis may be Friedel-Crafts acylation using propanoyl chloride to make 1-phenylpropan-1-one, followed by a Clemmensen reduction to obtain the final product.
18-29:
Answer: D
Nucleophilic Aromatic Substitution
18-30:
18-31:
18-32:
Possible route of synthesis:
Aromatic Substitutions Using Organometallic Reagents
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18-34:
Possible route of synthesis:
18-35:
Answer: D
Side-Chain Reactions of Benzene Derivatives
18-36:
18-37:
Answer: A
18-38: