Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 16, Problem 16.39P
(a)
Interpretation Introduction
Interpretation:
Show how the given drug can be synthesized by reductive amination of an appropriate
Concept Introduction:
Treatment of an aldehyde or ketone with ammonia or an amine in the presence of a reducing agent (like
Example:
(b)
Interpretation Introduction
Interpretation:
Show how the given drug can be synthesized by reductive amination of an appropriate aldehyde or ketone and amine.
Concept Introduction:
Treatment of an aldehyde or ketone with ammonia or an amine in the presence of a reducing agent (like
Example:
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Following are structural formulas for two more widely used sulfonylurea hypoglycemic agents.Show how each might be synthesized by converting an appropriate amine to a carbamic ester and then treating the carbamate with the sodium salt of a substituted benzenesulfonamide.
Show how to synthesize the following amines from the indicated starting materials below. Each of the final products may require several sequential steps. Draw the structure for each of the steps and show the reagents required.
Starting material
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b)
Benzene
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c)
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d)
benzene
p-bromoaniline + o-bromoaniline
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Chapter 16 Solutions
Organic Chemistry
Ch. 16.1 - Write the IUPAC name for each compound. Specify...Ch. 16.1 - Write structural formulas for all aldehydes with...Ch. 16.1 - Write the IUPAC name for each compound.Ch. 16.5 - Prob. 16.4PCh. 16.6 - Prob. 16.5PCh. 16.7 - Prob. 16.6PCh. 16.7 - Write a mechanism for the acid-catalyzed...Ch. 16.8 - Prob. 16.8PCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - The given mechanism of transamination reaction is...
Ch. 16.8 - The given mechanism of transamination reaction is...Ch. 16.8 - Prob. DQCh. 16.8 - Prob. EQCh. 16.8 - The given mechanism of transamination reaction is...Ch. 16.9 - Predict the position of the following equilibrium.Ch. 16.9 - Draw a structural formula for the keto form of...Ch. 16.10 - Prob. 16.11PCh. 16.11 - What aldehyde or ketone gives these alcohols upon...Ch. 16.11 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - The infrared spectrum of compound A, C6H12O, shows...Ch. 16 - Following are 1H-NMR spectra for compounds B...Ch. 16 - Draw structural formulas for the product formed by...Ch. 16 - Suggest a synthesis for the following alcohols...Ch. 16 - Show how to synthesize the following alcohol using...Ch. 16 - 1-Phenyl-2-butanol is used in perfumery. Show how...Ch. 16 - Prob. 16.22PCh. 16 - Draw structural formulas for (1) the...Ch. 16 - Show how to bring about the following conversions...Ch. 16 - Prob. 16.25PCh. 16 - Wittig reactions with the following -chloroethers...Ch. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - 5-Hydroxyhexanal forms a six-membered cyclic...Ch. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Propose a mechanism to account for the formation...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Show how to bring about the following conversion.Ch. 16 - A primary or secondary alcohol can be protected by...Ch. 16 - Prob. 16.37PCh. 16 - Prob. 16.38PCh. 16 - Prob. 16.39PCh. 16 - Prob. 16.40PCh. 16 - The following molecule belongs to a class of...Ch. 16 - When cis-2-decalone is dissolved in ether...Ch. 16 - Prob. 16.43PCh. 16 - Prob. 16.44PCh. 16 - The following bicyclic ketone has two -carbons and...Ch. 16 - Propose a mechanism for this reaction.Ch. 16 - The base-promoted rearrangement of an -haloketone...Ch. 16 - If the Favorskii rearrangement of...Ch. 16 - (R)-Pulegone, readily available from pennyroyal...Ch. 16 - (R)-Pulegone is converted to (R)-citronellic acid...Ch. 16 - Starting with cyclohexanone, show how to prepare...Ch. 16 - Show how to convert cyclopentanone to these...Ch. 16 - Prob. 16.53PCh. 16 - Prob. 16.54PCh. 16 - Prob. 16.55PCh. 16 - Following is the structural formula of Surfynol, a...Ch. 16 - Prob. 16.57PCh. 16 - Propose a mechanism for this isomerization.Ch. 16 - Starting with acetylene and 1-bromobutane as the...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - All rearrangements we have discussed so far have...Ch. 16 - In dilute aqueous base, (R)-glyceraldehyde is...Ch. 16 - Treatment of -D-glucose with methanol in the...Ch. 16 - Treating a Grignard reagent with carbon dioxide...Ch. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Write the products of the following sequences of...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Using your reaction roadmaps as a guide, show how...Ch. 16 - Prob. 16.78PCh. 16 - Prob. 16.79PCh. 16 - Prob. 16.80PCh. 16 - Prob. 16.81P
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Similar questions
- Show how to convert amines to other functional groups, and devise multistepsyntheses using amines as starting materials and intermediatesarrow_forwardusing the following medicinal drugs: redraw the chemical structures and label each functional group onto the structure a.) Inderal, a β-channelβ-channel blocker used to treat heart irregularities (propranolol) - for this one label the following: aromatic, ether, alcohol, amine b.) Ibuprofen, an anti-inflammatory agent - for this one label the following: aromatic, carboxylic acid c.) Aldomet (methyldopa) - for this one label the following: phenol, amine, carboxylic acidarrow_forwardWhat carboxylic acid and amine are needed to synthesize the pain reliever phenacetin? Phenacetin was once a component of the over-the-counter pain reliever APC (aspirin, phenacetin, caffeine), but it is no longer used because of its kidney toxicity.arrow_forward
- In the following reactions, compounds A and B are the major products obtained in each of them. Indicate the TRUE alternative: a) The reaction of A with ethanol allows obtaining an ester. b) The hydrolysis of A in an acidic medium allows obtaining a carboxylate ion and an amine. c) Reaction (II) is faster than reaction (I). d) The reaction of compound B with ammonia in ethanol allows obtaining an amide. e) Reaction (I) necessarily requires a catalyst.arrow_forwardBisphenol A is widely used as a building block in polymer synthesis and is found in the polycarbonate hard plastics of reusable drink containers, DVDs, cell phones, and other consumer goods. Bisphenol A is reported to have estrogenic activity, and its widespread occurrence in our environment is a potential concern. Describe one or two biochemical experiments that could be done to compare the activity of bisphenol A with that of its estradiol, its structural relative.arrow_forward
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