EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Chapter 11, Problem 11.64SP
Interpretation Introduction

To determine: The structures of Q, R and S and justification of structures by reaction.

Interpretation: The structures of Q, R and S; and justification of structures by reaction are to be stated.

Concept introduction: The dehydration of Q compound with dilute H2SO4, leads to the formation of optically active alkene C6H10, as enantiomers R and S. The ozonolysis of R alkene produces S, an optically active keto-aldehyde of formula C6H10O2.

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Which is the enantiomer of this molecule? NH2 (A) (C) B NH2 デ NH2 H- さ NH, (B) (D) H2N- H
Unknown Q is determined to have a molecular formula of C6H12O. Q is not optically active, and passing it through achiral column does not separate it into enantiomers. Q does not react with Br2, nor with cold, dilute KMnO4, nor doesit take up H2 under catalytic hydrogenation. Heating of Q with H2SO4 gives product R, of formula C6H10, which canbe separated into enantiomers. Ozonolysis of a single enantiomer of R produces S, an acyclic, optically active ketoaldehyde of formula C6H10O2. Propose structures for compounds Q, R, and S, and show how your structures would reactappropriately to give these results.
The chiral hydroxyl compound P, C7H14O contains a five-membered ring and showspositive result in iodoform test. Compound P and sodium bromide can be produced byrefluxing compound Q with aqueous NaOH solution. Compound P is heated withbenzoic acid in the presence of concentrated H2SO4 to form a sweet-smelling product,compound R. Deduce the structure of P, Q and R.   PLEASE PROVIDE CLEAR HAND WRITING AND SOLUTIONS

Chapter 11 Solutions

EP ORGANIC CHEMISTRY -MOD.MASTERING 18W

Ch. 11.6 - Predict the products of the following reactions....Ch. 11.7A - Propose a mechanism for the reaction of a....Ch. 11.7B - Prob. 11.13PCh. 11.7B - Show how you would use a simple chemical test to...Ch. 11.7C - Neopentyl alcohol, (CH3)3CCH2OH, reacts with...Ch. 11.7C - Prob. 11.16PCh. 11.7C - When cis-2-methylcyclohexanol reacts with the...Ch. 11.8 - Prob. 11.18PCh. 11.9 - Prob. 11.19PCh. 11.9 - Prob. 11.20PCh. 11.9 - Prob. 11.21PCh. 11.10A - Prob. 11.22PCh. 11.10A - Some alcohols undergo rearrangement or other...Ch. 11.10B - Prob. 11.24PCh. 11.10B - Explain why the acid-catalyzed condensation is a...Ch. 11.10B - Prob. 11.26PCh. 11.10B - When the following substituted cycloheptanol...Ch. 11.11A - Prob. 11.28PCh. 11.11A - Prob. 11.29PCh. 11.11B - Predict the products formed by periodic acid...Ch. 11.12 - Prob. 11.31PCh. 11.13A - Prob. 11.32PCh. 11.14 - Prob. 11.33PCh. 11.14 - a. Show how ethanol and cyclohexanol may be used...Ch. 11.14 - Prob. 11.35PCh. 11.14 - Phenols (pKa 10) are more acidic than other...Ch. 11.14 - To practice working through the early parts of a...Ch. 11.14 - Prob. 11.38PCh. 11 - Predict the major products of the following...Ch. 11 - Show how you would convert 2-methylcyclopentanol...Ch. 11 - In each case, show how you would synthesize the...Ch. 11 - Prob. 11.42SPCh. 11 - Prob. 11.43SPCh. 11 - Prob. 11.44SPCh. 11 - Both cis- and trans-2-methylcyclohexanol undergo...Ch. 11 - Prob. 11.46SPCh. 11 - Prob. 11.47SPCh. 11 - Show how you would make each compound, beginning...Ch. 11 - Predict the major products (including...Ch. 11 - Show how you would use simple chemical tests to...Ch. 11 - The compound shown below has three different types...Ch. 11 - Prob. 11.52SPCh. 11 - Prob. 11.53SPCh. 11 - Prob. 11.54SPCh. 11 - Prob. 11.55SPCh. 11 - Show how you would synthesize the following...Ch. 11 - Show how you would synthesize the following...Ch. 11 - The following pseudo-syntheses (guaranteed not to...Ch. 11 - Two unknowns, X and Y, both having the molecular...Ch. 11 - The Williamson ether synthesis involves the...Ch. 11 - Prob. 11.61SPCh. 11 - Prob. 11.62SPCh. 11 - Alcohols combine with ketones and aldehydes to...Ch. 11 - Prob. 11.64SPCh. 11 - Prob. 11.65SPCh. 11 - Prob. 11.66SP
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