Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 23, Problem 23.61P
Interpretation Introduction
Interpretation: The stepwise mechanism for the given reaction is to be stated. The reason corresponding to the fact that one stereogenic center changes configuration but the other does not is to be stated.
Concept introduction:
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Draw the structure of the acyclic polyhydroxy aldehyde that cyclizes to each hemiacetal.
Draw the structure of each molecule.
(a) 2,2-dimethylpropyl hex-3-ynoate;
(b) cyanoethanoic anhydride;
(c) cyanomethyl 5,5-dibromopentanoate;
(d) hex-3-ynoic anhydride;
(e) butyl (R)-4-carbamoylhexanoate
Treatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes configuration but the other does not.
Chapter 23 Solutions
Organic Chemistry-Package(Custom)
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
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
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- An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.arrow_forwardThe cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present atequilibrium. Will an aqueous solution of glucose reduce Tollens reagent and give a positive Tollens test? Explain.arrow_forwardDraw the structure (including stereochemistry) of the cyclic hemiacetal(s) formed when each hydroxy carbonyl compound is treated with aqueous acid.arrow_forward
- During the metabolism of glucose, glyceraldehyde 3-phosphate is converted to dihydroxyacetone phosphate by a process that involves two keto–enol tautomerizations. Draw a stepwise mechanism for this reaction in the presence of acid.arrow_forwardTreatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X. This reaction is the rst step in the synthesis of illudin-S, an antitumor substance isolated from the jack-o’-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?arrow_forwardHydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomers formed in this reaction from both A and B. Explain why this process gives an optically inactive product mixture from A and an optically active product mixture from B.arrow_forward
- An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers of each other.arrow_forwardAll are true or false a)In solution, glucose is in the cyclic acetal form only. b)The driving force for the Wittig reaction is the elimination of triphenylphosphine oxide c)1H NMR spectroscopy, you can tell the difference between an aldehyde and a ketone because an aldehyde has a proton signal between 9–10 ppm. d)When an aldehyde is reacted with excess ethanol with an acid as a catalyst it is called hemiacetal e) You can't use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone because the ketone will be protonated and thus unreactivearrow_forwardWhat happens when an unsymmetrical carbonyl compound like 2-methylcyclohexanone is treated with base?arrow_forward
- What product is formed when each compound undergoes anintramolecular reaction in the presence of acid?Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw thestereoisomers formed in this reaction from both A and B. Explain whythis process gives an optically inactive product mixture from A and anoptically active product mixture from B.arrow_forwardWhat enolate is formed when each ketone is treated with LDA in THF solution? What enolate is formed when these same ketones are treated with NaOCH3 in CH3OH solution?arrow_forwardTreatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from the jack-o'-lantern, a poisonous, saffron-colored mushroom. What is the structure of X?arrow_forward
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