Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 11, Problem 11.60SP
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Draw and Explain the reaction mechanism for the Williamson Ether reaction. Cresol is the nucleophilic component of the ether synthesis reaction and chloroacetic acid is the electrophilic component. Due to cresol being weak, a strong nucleophile has to be made before the reaction can begin. A base of KOH is added with cresol so that nucleophile can be strong before it is mixed with chloroacetic acid.
The anticoagulant Warfarin can be synthesized by a conjugate addition (Michael addition) reaction as shown below:
a) Propose a mechanism for the reaction starting from the enolate shown below. You can assume water is present for any proton transfers needed.b) We saw that the keto tautomer is normally preferred over the enol tautomer, however, the enol tautomer is present in the final product (Warfarin) and that is the more stable tautomer in this case. Why do you think the enol tautomer is more stable? Hint: consider the molecule as a whole.
Chapter 11 Solutions
Organic Chemistry (9th Edition)
Ch. 11.1 - Prob. 11.1PCh. 11.2C - Prob. 11.2PCh. 11.3 - Prob. 11.3PCh. 11.3 - Prob. 11.4PCh. 11.3 - Prob. 11.5PCh. 11.3 - Suggest the most appropriate method for each of...Ch. 11.4 - A chronic alcoholic requires a much larger dose of...Ch. 11.4 - Unlike ethylene glycol, propylene glycol...Ch. 11.5 - Predict the major products of the following...Ch. 11.5 - Show how you would convert propan-1-ol to the...
Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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- Provide the appropriate reagent(s) for the following transformationarrow_forwardDraw the reaction mechanism for the Williamson Ether reaction. Cresol is the nucleophilic component of the ether synthesis reaction and chloroacetic acid is the electrophilic component. Due to cresol being weak, a strong nucleophile has to be made before the reaction can begin. A base of KOH is added with cresol so that nucleophile can be strong before it is mixed with chloroacetic acid.arrow_forwardOCHEM Help with reactions Please provide the major product for A, B, and C of the following reaction...arrow_forward
- Provide synthetic schemes for the following transformationarrow_forwardDraw the mechanism with curved arrows (Williamson Ether Synthesis). Please provide detailed explanation of each step in sentences. I need to write a sentence based on each step.arrow_forwardFor the following synthetic scheme, draw the structure of the product of each reaction. Ignore stereochemistry for all structures.arrow_forward
- Please give the appropriate reagents FOR 1 AND 2 to complete the following synthesis.arrow_forwardA student uses a bromoacetic acid instead of a-cloroacetic acid for the Williamson Ether Synthesis reaction. which statements below are correct? (choose all that apply)arrow_forwardGive a clear handwritten answer..complete the following reaction with missing reagentsarrow_forward
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