ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Textbook Question
Chapter 17.12B, Problem 17.23P
Propose mechanisms and show the expected products of the following reactions.
- a. 2,4 - dinitrochlorobenzene + sodium methoxide (NaOCH3)
- b. 2,4 - dimethylchlorobenzene + sodium hydroxide, 350 °C
- c. p - nitrobromobenzene + methylamine(CH3- NH2)
- d. 2,4- dinitrochlorobenzene + excess hydrazine (H2N-NH2)
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X
Upon ozonolysis, Compound X produces two compounds: Compound Y and
Compound Z. Compound Y can also be prepared from the following synthetic
route:
PCC
1. R₂BH, THF
1. Mg. Et₂O
PCC
Compound Y
2.
CH₂Cl₂
2. NaOH, HO
CH₂Cl₂
3. H₂O*
From this information, draw the structures of Compounds X, Y, and Z. For
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just use hydrogens as the substituents.
Br
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You have achieved a preparation of para-chloroacetophenone from chlorobenzene
benzene
O CH3Br/AlBr3
O HBr
O
?
It remains to prepare chlorobenzene from benzene. Select the reagent that will prepare chlorobenzene from benzene.
O Br2
HNO3/H2SO4
O Cl₂/FeCl3
O CH3COCI/AICI 3
O Cl₂
O
O Zn(Hg)/HCI
O SO3/H2SO4
O KMnO4
O HCI
CICH2CH3/AICI 3
0
CH₂-C-CI
AICI,
CI
chlorobenzene
O
C-CH3
CI
para-chloroacetophenone
3.
cyclohexanone to cyclohexane.
A second year chemistry student is assigned a task to prepare compound 2 from
compound 1 using lithium aluminium hydride as a reducing agent. However, from the
reaction mixture, no traces of product 2 were detected. Explain this observation in detail
and suggest an alternative route that will lead to product 2.
H
1
CH3
LiAllH4
H
O:
2
CH3
que
Chapter 17 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
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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