Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
bartleby

Concept explainers

bartleby

Videos

Question
Book Icon
Chapter 23, Problem 23.63P
Interpretation Introduction

Interpretation: The stepwise mechanism for the given reaction is to be drawn.

Concept introduction: Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Blurred answer
Students have asked these similar questions
A key step in the synthesis of β-vetivone, a major constituent of vetiver, a perennial grass found in tropical and subtropical regions of the world, involved the reaction of compound A and dihalide B with two equivalents of LDA to form C. Draw a stepwise mechanism for this reaction. β-Vetivone contains a spiro ring system—that is, two rings that share a single carbon atom.
One step in the synthesis of the antihistamine fexofenadine involves acid-catalyzed hydration of the triple bond in A. Draw a stepwise mechanism for this reaction and explain why only ketone B is formed.
Draw a stepwise mechanism for the conversion of lactone A to ester B using HCl in ethanol. B is converted in one step to ethyl chrysanthemate, a useful intermediate in the synthesis of a variety of pyrethrins, naturally occurring insecticides with three-membered rings that are isolated from chrysanthemums.

Chapter 23 Solutions

Organic Chemistry

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
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY