Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 22, Problem 22.37P
Rank the following compounds in order of increasing reactivity in nucleophilic acyl substitution.
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Chapter 22 Solutions
Organic Chemistry-Package(Custom)
Ch. 22 - Prob. 22.1PCh. 22 - Draw the three possible resonance structures for...Ch. 22 - Prob. 22.3PCh. 22 - Give an IUPAC or common name for each compound.Ch. 22 - Problem 22.5 Draw the structure corresponding to...Ch. 22 - Prob. 22.6PCh. 22 - How would the compounds in each pair differ in...Ch. 22 - Problem 22.8 Deduce the structures of compounds ...Ch. 22 - Prob. 22.9PCh. 22 - Rank the compounds in each group in order of...
Ch. 22 - Prob. 22.11PCh. 22 - Prob. 22.12PCh. 22 - Prob. 22.13PCh. 22 - Prob. 22.14PCh. 22 - Problem 22.15 Draw the products of each...Ch. 22 - Problem 22.16 Draw the products of each reaction.
...Ch. 22 - Prob. 22.17PCh. 22 - Problem 22.18 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.19PCh. 22 - Problem 22.20 Fenofibrate is a...Ch. 22 - Problem 22.21 What product is formed when the...Ch. 22 - How would you synthesize olestra from sucrose?
Ch. 22 - What is the composition of the soap prepared by...Ch. 22 - Problem 22.24 Draw a stepwise mechanism for the...Ch. 22 - Prob. 22.25PCh. 22 - Problem 22.26 Some penicillins cannot be...Ch. 22 - Prob. 22.27PCh. 22 - Prob. 22.28PCh. 22 - Prob. 22.29PCh. 22 - Problem 22.30 Glucosamine is a dietry supplement...Ch. 22 - Draw the products of each reaction. a. c. b.Ch. 22 - Draw a tautomer of each compound.Ch. 22 - Draw the product of each reaction. a.b.Ch. 22 - Draw the product of each reaction. a. b.Ch. 22 - Prob. 22.35PCh. 22 - Problem 22.36 Outline two different ways that can...Ch. 22 - 22.37 Rank the following compounds in order of...Ch. 22 - Prob. 22.38PCh. 22 - Prob. 22.39PCh. 22 - Prob. 22.40PCh. 22 - Give thestructure corresponding to each name. a....Ch. 22 - Prob. 22.42PCh. 22 - Prob. 22.43PCh. 22 - 22.43 Explain why is a stronger acid and a weaker...Ch. 22 - Draw the product formed when pentanoyl chloride...Ch. 22 - Draw the product formed when pentanoic anhydride...Ch. 22 - Draw the product formed when phenylacetic acid is...Ch. 22 - Prob. 22.48PCh. 22 - Prob. 22.49PCh. 22 - Draw the product formed when phenylacetonitrile ...Ch. 22 - Prob. 22.51PCh. 22 - Prob. 22.52PCh. 22 - Prob. 22.53PCh. 22 - Prob. 22.54PCh. 22 - Prob. 22.55PCh. 22 - Prob. 22.56PCh. 22 - Draw a stepwise mechanism for each reaction. a. b.Ch. 22 - When acetic acid CH3COOH is treated with a trace...Ch. 22 - Prob. 22.59PCh. 22 - Prob. 22.60PCh. 22 - Prob. 22.61PCh. 22 - Prob. 22.62PCh. 22 - Prob. 22.63PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - 22.63 Acid-catalyzed hydrolysis of forms compound...Ch. 22 - Prob. 22.66PCh. 22 - Devise a synthesis of each compound using...Ch. 22 - Convert 1-bromohexane (CH3CH2CH2CH2CH2CH2Br) into...Ch. 22 - Prob. 22.69PCh. 22 - Prob. 22.70PCh. 22 - Prob. 22.71PCh. 22 - Prob. 22.72PCh. 22 - Prob. 22.73PCh. 22 - Prob. 22.74PCh. 22 - Devise a synthesis of each labeled compound using...Ch. 22 - 22.70 What polyester or poly amide can be prepared...Ch. 22 - 22.71 What two monomers are needed to prepare each...Ch. 22 - Prob. 22.78PCh. 22 - How can IR spectroscopy be used to distinguish...Ch. 22 - Rank the compounds in each group in order of...Ch. 22 - 22.75 Identify the structures of each compound...Ch. 22 - 22.76 Identify the structures of A and B, isomers...Ch. 22 - Prob. 22.83PCh. 22 - 22.78 Identify the structure of compound C...Ch. 22 - 22.79 Identify the structures of D and E, isomers...Ch. 22 - 22.80 With reference to amides A and B, the...Ch. 22 - Prob. 22.87PCh. 22 - Prob. 22.88PCh. 22 - Prob. 22.89PCh. 22 - Draw a stepwise mechanism for the following...Ch. 22 - Draw a stepwise mechanism for the following...
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- Arrange the following CARBONYL compounds (INCREASING REACTIVITY towards NUCLEOPHILIC ADDITION)arrow_forwardWhich of the following compounds will react with methylamine to form the imine shown below? N.arrow_forwardRank the following compounds in order of increasing reactivity towards nucleophilic addition (most to least reactive). Provide a brief explanation for your choice. i) H ii) H iii) CH3arrow_forward
- Consider carbonyl compounds A–E drawn below. (a) Rank A–E in order of increasing stability. (b) Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid. (c) Which compound is most reactive in nucleophilic addition?arrow_forwardProvide an explanation (in detail) on how base catalysts speed up nucleophilic reactions of carbonyl compounds.arrow_forwardDraw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. CH3COCl, AlCl3arrow_forward
- Ibufenac, a para-disubstituted arene with the structure HO2CCH2C6H4CH2CH(CH3)2, is a much more potent analgesic than aspirin, but it was never sold commercially because it caused liver toxicity in some clinical trials. Devise a synthesis of ibufenac from benzene and organic halides having fewer than five carbons.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forwardIdentify the lettered compounds in each reaction sequence.Draw the product formed when phenylacetonitrile (C6H5CH2CN) istreated with below reagent. H2O, −OHarrow_forward
- When (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH,nucleophilic substitution yields an optically inactive solution. When theisomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OHunder the same conditions, nucleophilic substitution forms an opticallyactive solution. Draw the products formed in each reaction, and explainwhy the difference in optical activity is observed.arrow_forwardIdentify the missing reagents a-f in the following scheme:arrow_forwardThe ether, CH3OCH2CH3, can be prepared by two different nucleophilic substitution reactions, one using CH3O- as nucleophile and the other using CH3CH2O- as nucleophile. Draw both routes.arrow_forward
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