Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 21, Problem 21.87P
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β-D-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with CH3OH in the presence of acid. Draw a stepwise mechanism for this reaction. Explain why two acetals are formed from a single starting material.
Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with each reagent. With some reagents, no reaction occurs.
NaHCO3
β-D-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with CH3OH in the presence of acid. Draw a stepwise mechanism for this reaction. Explain why two acetals are formed from a single starting material.
Chapter 21 Solutions
Organic Chemistry-Package(Custom)
Ch. 21 - Rank the following compounds in order of...Ch. 21 - Prob. 21.2PCh. 21 - Give the IUPAC name for each aldehyde.Ch. 21 - Prob. 21.4PCh. 21 - Give the IUPAC name for each ketone.Ch. 21 - Prob. 21.6PCh. 21 - Prob. 21.7PCh. 21 - The boiling point of is significantly higher than...Ch. 21 - Which carbonyl group in each pair absorbs at a...Ch. 21 - Problem 21.10 Draw the structure of all...
Ch. 21 - Prob. 21.11PCh. 21 - Prob. 21.12PCh. 21 - Prob. 21.13PCh. 21 - Prob. 21.14PCh. 21 - Problem 21.15 Draw the product of each...Ch. 21 - Prob. 21.16PCh. 21 - Prob. 21.17PCh. 21 - Outline a synthesis of each Wittig reagent from...Ch. 21 - Draw the products including stereoisomers formed...Ch. 21 - Prob. 21.20PCh. 21 - Prob. 21.21PCh. 21 - Show two methods to synthesize each alkene: a...Ch. 21 - Problem 21.22 The product formed when reacts with...Ch. 21 - What 1 amine and carbonyl compound are needed to...Ch. 21 - Prob. 21.25PCh. 21 - Prob. 21.26PCh. 21 - Prob. 21.27PCh. 21 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.29 Draw the products of each...Ch. 21 - Problem 21.30 Label each compound as an acetal, a...Ch. 21 - Problem 21.31 Draw a stepwise mechanism for the...Ch. 21 - Problem 21.32 Draw the products of each...Ch. 21 - Problem 21.33 Safrole is a naturally occurring...Ch. 21 - Problem 21.35 How would you use a protecting group...Ch. 21 - Prob. 21.35PCh. 21 - Problem 21.37 Two naturally occurring compounds...Ch. 21 - Problem 21.38 Draw the products of each...Ch. 21 - Prob. 21.38PCh. 21 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 21 - 21.41 Rank the following compounds in order of...Ch. 21 - Prob. 21.41PCh. 21 - Give the IUPAC name for each compound. a. d. g. b....Ch. 21 - Give the structure corresponding to each name. a....Ch. 21 - Including stereoisomers, draw the 11 aldehydes...Ch. 21 - Prob. 21.45PCh. 21 - Prob. 21.46PCh. 21 - What alkyl halide is needed to prepare each Wittig...Ch. 21 - 21.46 Draw the products of each reaction.
a. e....Ch. 21 - Prob. 21.49PCh. 21 - Prob. 21.50PCh. 21 - Prob. 21.51PCh. 21 - Prob. 21.52PCh. 21 - Prob. 21.53PCh. 21 - Rank the following compounds in order of...Ch. 21 - Which compound forms the higher concentration of...Ch. 21 - Prob. 21.56PCh. 21 - What Wittig reagent and carbonyl compound are...Ch. 21 - Prob. 21.58PCh. 21 - What reagents are needed to convert each compound...Ch. 21 - What reagents are needed to convert each compound...Ch. 21 - Prob. 21.61PCh. 21 - Devise a synthesis of each alkene using a Wittig...Ch. 21 - Devise a synthesis of each compound from...Ch. 21 - Prob. 21.64PCh. 21 - Prob. 21.65PCh. 21 - Prob. 21.66PCh. 21 - Prob. 21.67PCh. 21 - Prob. 21.68PCh. 21 - Prob. 21.69PCh. 21 - 21.64 Draw a stepwise mechanism for the following...Ch. 21 - 21.65 Draw a stepwise mechanism f or the following...Ch. 21 - Prob. 21.72PCh. 21 - 21.67 Draw a stepwise mechanism for each...Ch. 21 - 21.68 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.75PCh. 21 - Prob. 21.76PCh. 21 - Prob. 21.77PCh. 21 - Prob. 21.78PCh. 21 - Prob. 21.79PCh. 21 - 21.73 Although the carbonyl absorption of cyclic...Ch. 21 - 21.74 Use the and data to determine the...Ch. 21 - 21.75 A solution of acetone in ethanol in the...Ch. 21 - Compounds A and B have molecular formula ....Ch. 21 - 21.77 An unknown compound C of molecular formula ...Ch. 21 - 21.78 An unknown compound D exhibits a strong...Ch. 21 - Prob. 21.86PCh. 21 - -D-Glucose, a hemiacetal, can be converted to a...Ch. 21 - 21.81 Draw a stepwise mechanism for the following...Ch. 21 - Prob. 21.89PCh. 21 - Prob. 21.90PCh. 21 - Prob. 21.91PCh. 21 - 21.86 Draw stepwise mechanism for the following...
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- Draw a stepwise mechanism for the following reaction in (a) aacid-catalyzed and (b) base-catalyzed hydration.arrow_forwardB-D-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with CH,OH in the presence of acid. Draw a stepwise mechanism for this reaction. Explain why two acetals are formed from a single starting material. он он OH CH;OH, HCI HO Но HO HO но + Но + H20 OH OCH3 OH OHOCHS но B-D-glucosearrow_forwardDraw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. NaOHarrow_forward
- Draw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. CH3COCl, AlCl3arrow_forwardDraw the product(s) formed when A is treated with following reagent. LiAlH4, then H2Oarrow_forwardDraw the product(s) formed when A is treated with each reagent. (a) NaBH4, CH3OH (b) [1] LiAlH4; [2] H2O (c) CH3CH2MgBr; [2] H2Oarrow_forward
- Draw the products formed when p-methylaniline (p-CH3C6H4NH2) istreated with following reagent. HClarrow_forwardAnswer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.a.In Chapter 11, we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols. b.Explain why the enol O—H proton is more acidic than an alcohol O—H proton. c. Why is curcumin colored? d.Explain why curcumin is an antioxidant.arrow_forwardDraw the product formed when pentanal (CH3CH2CH2CH2CHO) is treatedwith following reagent. With some reagents, no reaction occurs. [1] HC≡CNa; [2] H2Oarrow_forward
- Dimethyl cyclopropanes can be prepared by the reaction of an α, β-unsaturated carbonyl compound X with two equivalents of a Wittigreagent Y. Draw a stepwise mechanism for this reaction.arrow_forwardTwo naturally occurring compounds that contain stable cyclic hemiacetals and acetals are monensin and digoxin. Monensin, a polyether antibiotic produced by Streptomyces cinnamonensis, is used as an additive in cattle feed. Digoxin is a widely prescribed cardiac drug used to increase the force of heart contractions. Label each acetal, hemiacetal, and ether in both compounds.arrow_forwardDraw the product formed when each organometallic reagent is treated with H2O.arrow_forward
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