ORGANIC CHEMISTRY W/OWL
ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
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Chapter 19.SE, Problem 37MP
Interpretation Introduction

Interpretation:

A mechanism for the formation of an acetal when α-glucose is treated with an acid catalyst is to be proposed. The structure of the stereoisomeric acetal that can be expected as a product also is to be given.

Concept introduction:

The acid will protonate one of the –OH groups in glucose. An internal nucleophilic attack of the oxygen present will eliminate water to produce an alkene. The addition of methanol to alkenes can take place from both sides of the planar double bond leading to the formation of two stereomeric acetals one woth axial –OCH3 and other with equtorial –OCH3.

To propose:

A mechanism for the formation of an acetal when α-glucose is treated with an acid catalyst and to give the structure of the stereoisomeric acetal that can be expected as a product.

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Chapter 19 Solutions

ORGANIC CHEMISTRY W/OWL

Ch. 19.8 - Prob. 11PCh. 19.8 - Prob. 12PCh. 19.9 - Prob. 13PCh. 19.10 - Prob. 14PCh. 19.10 - Prob. 15PCh. 19.11 - What carbonyl compound and what phosphorus ylide...Ch. 19.11 - -Carotene, a yellow food-coloring agent and...Ch. 19.12 - Prob. 18PCh. 19.12 - Prob. 19PCh. 19.13 - Prob. 20PCh. 19.13 - Treatment of 2-cyclohexenone with HCN/KCN yields a...Ch. 19.13 - How might conjugate addition reactions of lithium...Ch. 19.14 - How might you use IR spectroscopy to determine...Ch. 19.14 - Prob. 24PCh. 19.14 - Prob. 25PCh. 19.14 - Prob. 26PCh. 19.SE - Each of the following substances can be prepared...Ch. 19.SE - Prob. 28VCCh. 19.SE - Prob. 29VCCh. 19.SE - Prob. 30MPCh. 19.SE - Prob. 31MPCh. 19.SE - Prob. 32MPCh. 19.SE - Prob. 33MPCh. 19.SE - Prob. 34MPCh. 19.SE - Prob. 35MPCh. 19.SE - It is not uncommon for organic chemists to prepare...Ch. 19.SE - Prob. 37MPCh. 19.SE - Prob. 38MPCh. 19.SE - Prob. 39MPCh. 19.SE - Prob. 40MPCh. 19.SE - Aldehydes and ketones react with thiols to yield...Ch. 19.SE - Prob. 42MPCh. 19.SE - When cyclohexanone is heated in the presence of a...Ch. 19.SE - Prob. 44MPCh. 19.SE - The Meerwein-Ponndorf-Verley reaction involves...Ch. 19.SE - Propose a mechanism to account for the formation...Ch. 19.SE - Prob. 47MPCh. 19.SE - Prob. 48MPCh. 19.SE - Treatment of an , -unsaturated ketone with basic...Ch. 19.SE - Prob. 50MPCh. 19.SE - Prob. 51MPCh. 19.SE - Prob. 52MPCh. 19.SE - Prob. 53MPCh. 19.SE - Prob. 54APCh. 19.SE - Draw and name the seven aldehydes and ketones with...Ch. 19.SE - Give IUPAC names for the following compounds:Ch. 19.SE - Draw structures of compounds that fit the...Ch. 19.SE - Predict the products of the reaction of (1)...Ch. 19.SE - Show how you might use a Wittig reaction to...Ch. 19.SE - How would you use a Grignard reaction on an...Ch. 19.SE - Prob. 61APCh. 19.SE - Prob. 62APCh. 19.SE - How would you synthesize the following substances...Ch. 19.SE - Carvone is the major constituent of spearmint oil....Ch. 19.SE - How would you synthesize the following compounds...Ch. 19.SE - At what position would you expect to observe IR...Ch. 19.SE - Acidcatalyzed dehydration of...Ch. 19.SE - Choose the structure that best fits the IR...Ch. 19.SE - Propose structures for molecules that meet the...Ch. 19.SE - Prob. 70APCh. 19.SE - Prob. 71APCh. 19.SE - When 4hydroxybutanal is treated with methanol in...Ch. 19.SE - Prob. 73APCh. 19.SE - Prob. 74APCh. 19.SE - Prob. 75APCh. 19.SE - Prob. 76APCh. 19.SE - Prob. 77APCh. 19.SE - Tamoxifen is a drug used in the treatment of...Ch. 19.SE - Compound A, MW 86, shows an IR absorption at 1730...Ch. 19.SE - Compound B is isomeric with A (Problem 19-79) and...Ch. 19.SE - The 1HNMR spectrum shown is that of a compound...Ch. 19.SE - Prob. 82APCh. 19.SE - Propose structures for ketones or aldehydes that...Ch. 19.SE - Prob. 84APCh. 19.SE - Prob. 85APCh. 19.SE - The proton and carbon NMR spectra for each of...Ch. 19.SE - The proton NMR spectrum for a compound with...
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