Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 23, Problem 23.75P
Interpretation Introduction
Interpretation: The stepwise mechanism for the given reaction is to be devised.
Concept introduction: The organic compound having conjugated diene and keto group are classified as dienone. The dienone undergoes rearrangement in presence of acid to form stable phenol derivative. This rearrangement is known as dienone-phenol rearrangement.
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SYNTHESIS REACTIONS. For the following reactions, synthesize the given products from the given reactants.
Multiple reactions/steps will be needed. For the one of the steps (ie reactions) in each synthesis, write out the
mechanism for that reaction and draw an energy diagram showing the correct number of hills and valleys for
that step's mechanism.
CI
b.
a.
Use acetylene (ethyne)
and any alkyl halide as
your starting materials
Br
C.
d.
"OH
OH
III.
OH
Chapter 23 Solutions
Organic Chemistry
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
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