Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Question
Chapter 5, Problem 5.16P
Interpretation Introduction
Interpretation:
The formation of three given ozonides from
Concept introduction:
Ozonolysis of
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4. (A) A medicinal chemist wished to make a series of aromatic molecules bearing a ketone and
thioether group with ortho, meta, or para relationships. To achieve this, they propose using
nucleophilic aromatic substitution treating the corresponding ortho, meta, and para aryl
chlorides with sodium ethanethiolate (NaSEt). Predict which of these reactions will likely
work and which will likely fail. Provide a mechanistic explanation why.
SET O
NasEt
EtS
glagol Glal ol
heat
EtS
target molecules
EtS
(B) Would the analogous reactions using EtMgBr instead of NaSEt be more or less likely to work?
Explain why or why not.
لمسلم
EtMgBr
(i)
The enolisation of ketone A can generate an equilibrium mixture of A and either enol B or
enolate C. Give the structure of both B and C, and the mechanism for their formation from A
under the given conditions.
(ii)
A
HCI (cat.)
NaOH (cat.)
B
с
Draw the structure of the product obtained when A is dissolved in D3O*. Give a detailed
mechanism to account for the structure you propose.
(a) How will you obtain the following :(i) Benzaldehyde from Phenol (ii) Benzoic acid from Aniline(b) Give reasons :(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 5.1PCh. 5 - Prob. 5.2PCh. 5 - Prob. 5.3PCh. 5 - Prob. 5.4PCh. 5 - Prob. 5.5PCh. 5 - Prob. 5.6PCh. 5 - Prob. 5.7PCh. 5 - Prob. 5.8PCh. 5 - Prob. 5.9PCh. 5 - Prob. 5.10P
Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27APCh. 5 - Prob. 5.28APCh. 5 - Prob. 5.29APCh. 5 - Prob. 5.30APCh. 5 - Prob. 5.31APCh. 5 - Prob. 5.32APCh. 5 - Prob. 5.33APCh. 5 - Prob. 5.34APCh. 5 - Prob. 5.35APCh. 5 - Prob. 5.36APCh. 5 - Prob. 5.37APCh. 5 - Prob. 5.38APCh. 5 - Prob. 5.39APCh. 5 - Prob. 5.40APCh. 5 - Prob. 5.41APCh. 5 - Prob. 5.42APCh. 5 - Prob. 5.43APCh. 5 - Prob. 5.44APCh. 5 - Prob. 5.45APCh. 5 - Prob. 5.46APCh. 5 - Prob. 5.47APCh. 5 - Prob. 5.48APCh. 5 - Prob. 5.49APCh. 5 - Prob. 5.50APCh. 5 - Prob. 5.51APCh. 5 - Prob. 5.52APCh. 5 - Prob. 5.53APCh. 5 - Prob. 5.54AP
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- Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.arrow_forward(d) Propose a reaction mechanism to account for the following reaction. AIC3arrow_forwardPLEASE ANSWER PART (II) ONLY GIVE STEP BY STEP MECHANISM WITH BRIEF EXPLANATIONarrow_forward
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