N,N -Diethyl- m -toluamide (DEET) is the active ingredient in several common insect repellents. Propose a synthesis for DEET from 3-methylbenzoic acid.
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Organic Chemistry
8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
BuyFindlaunch
Organic Chemistry
8th Edition
William H. Brown + 3 others
Publisher: Cengage Learning
ISBN: 9781305580350
Solutions
Chapter 18, Problem 18.35P
Textbook Problem
N,N-Diethyl-m-toluamide (DEET) is the active ingredient in several common insect repellents. Propose a synthesis for DEET from 3-methylbenzoic acid.
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Organic Chemistry
Ch. 18.1 - Draw a structural formula for each compound. (a)...Ch. 18.2 - Will phthalimide dissolve in aqueous sodium...Ch. 18.4 - Complete and balance equations for the hydrolysis...Ch. 18.4 - Complete equations for the hydrolysis of the...Ch. 18.4 - Synthesis of nitriles by nucleophilic displacement...Ch. 18.5 - Complete the following transesterification...Ch. 18.6 - Complete and balance equations for the following...Ch. 18.8 - A common mechanism of resistance in bacteria...Ch. 18.8 - Several compounds have been found to inhibit...Ch. 18.8 - The formation of the amide that is not part of the...
Ch. 18.8 - The following sequence of steps is used to create...Ch. 18.9 - Show how to prepare each alcohol by treating an...Ch. 18.9 - Show how to bring about each conversion in good...Ch. 18.10 - Show how to convert hexanoic acid to each amine.Ch. 18.10 - Show how to convert (R)-2-phenylpropanoic acid to...Ch. 18 - Draw a structural formula for each compound. (a)...Ch. 18 - Write the IUPAC name for each compound. (a)...Ch. 18 - Both the melting point and boiling point of...Ch. 18 - Each hydrogen of a primary amide typically has a...Ch. 18 - Propose a structural formula for compound A,...Ch. 18 - Propose a structural formula for compound B,...Ch. 18 - Propose a structural formula for each compound...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Draw a structural formula of the principal product...Ch. 18 - The mechanism for hydrolysis of an ester in...Ch. 18 - Predict the distribution of oxygen-18 in the...Ch. 18 - Draw a structural formula for the principal...Ch. 18 - Draw a structural formula of the principal product...Ch. 18 - Show the product expected when the following...Ch. 18 - The reagent diisobutylaluminum hydride (DIBALH)...Ch. 18 - Show the product of treating this anhydride with...Ch. 18 - The analgesic acetaminophen is synthesized by...Ch. 18 - Treating choline with acetic anhydride gives...Ch. 18 - Nicotinic acid, more commonly named niacin, is one...Ch. 18 - Complete each reaction.Ch. 18 - Show the product of treating -butyrolactone with...Ch. 18 - Show the product of treating the following -lactam...Ch. 18 - Draw structural formulas for the products of...Ch. 18 - N,N-Diethyl-m-toluamide (DEET) is the active...Ch. 18 - Isoniazid, a drug used to treat tuberculosis, is...Ch. 18 - Show how to convert phenylacetylene to allyl...Ch. 18 - A step in a synthesis of PGE1 (prostaglandin E1,...Ch. 18 - Barbiturates are prepared by treating a derivative...Ch. 18 - The following compound is one of a group of...Ch. 18 - Show how to synthesize 5-nonanone from...Ch. 18 - Procaine (its hydrochloride is marketed as...Ch. 18 - The following sequence of steps converts...Ch. 18 - Reaction of a primary or secondary amine with...Ch. 18 - Several sulfonylureas, a class of compounds...Ch. 18 - Following are structural formulas for two more...Ch. 18 - Amantadine is effective in preventing infections...Ch. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Following is a retrosynthetic analysis for the...Ch. 18 - Given this retrosynthetic analysis, propose a...Ch. 18 - Propose a synthesis for diphenhydramine starting...Ch. 18 - Propose a synthesis of the topical anesthetic...Ch. 18 - Following is an outline of a synthesis of...Ch. 18 - In Problem 7.28, we saw this step in Johnsons...Ch. 18 - Using the principles for writing mechanisms and...Ch. 18 - The following statements are true experimental...Ch. 18 - We have seen two methods for converting a...Ch. 18 - Using the same reasoning as in Problem 18.58, show...Ch. 18 - A urethane is a molecule in which a carbonyl group...Ch. 18 - Suppose that you start with a diisocyanate and a...Ch. 18 - Use the reaction roadmap roadmap you made for...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Using your reaction roadmap as a guide, show how...Ch. 18 - Minoxidil is a molecule that causes hair growth in...Ch. 18 - Chloroformates have the functional group , in...Ch. 18 - Acid anhydrides are often used in place of acid...Ch. 18 - The benzyl ether group (OBn) is often used as a...
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