ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 26.2P
Interpretation Introduction
Interpretation: Reagents A and B are to be predicted.
Concept introduction: Organocuprate reagents
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Provide the reagents necessary to complete the following
synthesis.
?
pp
The two reactions that follow involve nucleophilic substitution at an acyl carbon.
For each reaction, show the electrophile and the nucleophile in the key bond-
forming step, the corresponding tetrahedral addition intermediate, and the leaving
group in the bond-breaking step. Write a general mechanistic scheme (use curved
arrows to show bond-making and bond-breaking processes) for these reactions,
keeping in mind that acid- and base-catalyzed processes will differ in their timing
of proton transfers.
00
|| ||
PhCOCPh+ C₂H5OH
00
||||
PhCOCPh+ 2 CH3NH
H₂SO4 cat.
O
PhCOC₂H5+ PhCO₂H
PhCNCHg + CH3NH PhCO
Chapter 26 Solutions
ORGANIC CHEMISTRY
Ch. 26 - Prob. 26.1PCh. 26 - Prob. 26.2PCh. 26 - Prob. 26.3PCh. 26 - Prob. 26.4PCh. 26 - Prob. 26.5PCh. 26 - Prob. 26.6PCh. 26 - Prob. 26.7PCh. 26 - Problem 26.8
What starting materials are needed to...Ch. 26 - Prob. 26.9PCh. 26 - Problem 26.10
What reagents are needed to convert...
Ch. 26 - Problem 26.11
What product is formed when each...Ch. 26 - Prob. 26.12PCh. 26 - Problem 26.13
Draw the products formed when each...Ch. 26 - Problem 26.14
What products are formed when ...Ch. 26 - Problem 26.15
Draw the product formed from...Ch. 26 -
What product is formed by ring-closing metathesis...Ch. 26 - Problem 26.17
What starting material is needed to...Ch. 26 - 26.18 In addition to organic halides, alkyl...Ch. 26 - 26.19 What product is formed by ring-closing...Ch. 26 - 26.20 Draw the products formed in each...Ch. 26 - What organic halide is needed to convert lithium...Ch. 26 - 26.22 How can you convert ethynylcyclohexane to...Ch. 26 - 26.23 What compound is needed to convert styrene...Ch. 26 - 26.24 What steps are needed to convert to octane...Ch. 26 - Prob. 26.25PCh. 26 - Prob. 26.26PCh. 26 - 26.27 Draw the products (including stereoisomers)...Ch. 26 - 26.28 Treatment of cyclohexene with and forms...Ch. 26 - Prob. 26.29PCh. 26 - 26.30 What starting material is needed to prepare...Ch. 26 - Prob. 26.31PCh. 26 - Prob. 26.32PCh. 26 - When certain cycloalkenes are used in metathesis...Ch. 26 - 26.34 Draw the products formed in each reaction.
...Ch. 26 - Prob. 26.35PCh. 26 - Draw a stepwise mechanism for the following...Ch. 26 - Sulfur ylides, like the phosphorus ylides of...Ch. 26 - Although diazomethane is often not a useful...Ch. 26 - Prob. 26.39PCh. 26 - Prob. 26.40PCh. 26 - Prob. 26.41PCh. 26 - Prob. 26.42PCh. 26 - 26.43 Devise a synthesis of each compound using a...Ch. 26 - 26.44 Devise a synthesis of each compound from...Ch. 26 - 26.45 Devise a synthesis of each compound from...Ch. 26 - 26.46 Devise a synthesis of each substituted...Ch. 26 - Biaryls, compounds containing two aromatic rings...Ch. 26 - Prob. 26.48PCh. 26 - 26.49 Draw the product formed from the...Ch. 26 - Prob. 26.50PCh. 26 - 26.51 Devise a synthesis of each of the following...Ch. 26 - Prob. 26.52PCh. 26 - 26.53 The following conversion, carried out in the...Ch. 26 - Prob. 26.54PCh. 26 - 26.55 Dimethyl cyclopropanes can be prepared by...Ch. 26 - Prob. 26.56P
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