ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
Question
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Chapter 8, Problem 8.54SP

(a)

Interpretation Introduction

To determine: The product from the given reaction.

Interpretation: The given question stated that Professor Patrick Dussault has developed an alternative to the standard two step ozonolysis procedure requires reduction of the ozonide in a second step. Pyridine is used as a basic organic solvent in a one step process. The desired product from the given reaction is to be predicted.

Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where C=C bond breaks and hence formation of CO bond takes place. During oxidative cleavage, ketone or aldehyde formation takes place.

(b)

Interpretation Introduction

To determine: The major product of the given reaction.

Interpretation: The major product of the given reaction is to be predicted

Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where C=C bond breaks and hence formation of CO bond takes place. During oxidative cleavage, ketone or aldehyde formation takes place.

(c)

Interpretation Introduction

To determine: The major product of the given reaction.

Interpretation: The major product of the given reaction is to be predicted.

Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where C=C bond breaks and hence formation of CO bond takes place. During oxidative cleavage, ketone or aldehyde formation takes place.

(d)

Interpretation Introduction

To determine: The major product of the given reaction.

Interpretation: The major product of the given reaction is to be predicted.

Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where C=C bond breaks and hence formation of CO bond takes place. During oxidative cleavage, ketone or aldehyde formation takes place.

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Provide the reagents for the short syntheses (about 3-4 steps).
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Predict the major organic product of the following reaction sequence. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 h. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over NazSO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143-1146.)

Chapter 8 Solutions

ORGANIC CHEMISTRY MASTERINGCHEM ACCESS

Ch. 8.7A - Prob. 8.11PCh. 8.7C - Prob. 8.12PCh. 8.7C - Prob. 8.13PCh. 8.7C - a. When (Z)-3-methylhex-3-ene undergoes...Ch. 8.7C - Prob. 8.15PCh. 8.7C - Prob. 8.16PCh. 8.8B - Prob. 8.17PCh. 8.8B - Prob. 8.18PCh. 8.9 - Prob. 8.19PCh. 8.9 - Prob. 8.20PCh. 8.9 - Prob. 8.21PCh. 8.9 - Prob. 8.22PCh. 8.10 - Prob. 8.23PCh. 8.10 - Prob. 8.24PCh. 8.10 - Prob. 8.25PCh. 8.11A - Prob. 8.26PCh. 8.11B - Prob. 8.27PCh. 8.11B - Prob. 8.28PCh. 8.12 - Prob. 8.29PCh. 8.13 - a. Propose a mechanism for the conversion of...Ch. 8.13 - Magnesium monoperoxyphthalate (MMPP) epoxidizes...Ch. 8.13 - Predict the major products of the following...Ch. 8.13 - When 1,2-epoxycyclohexane (cyclohexene oxide) is...Ch. 8.14C - Predict the major products of the following...Ch. 8.14C - Prob. 8.35PCh. 8.15B - Prob. 8.36PCh. 8.15C - Predict the major products of the following...Ch. 8.16A - Prob. 8.38PCh. 8.16A - Prob. 8.39PCh. 8.16B - Prob. 8.40PCh. 8.16B - Prob. 8.41PCh. 8.16C - Prob. 8.42PCh. 8.17B - Prob. 8.43PCh. 8.17B - Prob. 8.44PCh. 8.17B - Show how you would synthesize each compound,...Ch. 8 - Prob. 8.46SPCh. 8 - Prob. 8.47SPCh. 8 - Give the products expected when the following...Ch. 8 - Show how you would make the following compounds...Ch. 8 - Using 1,2-dimethylcyclohexene as your starting...Ch. 8 - Show how you would synthesize each compound using...Ch. 8 - Prob. 8.52SPCh. 8 - Show how you might use olefin metathesis to...Ch. 8 - Prob. 8.54SPCh. 8 - Prob. 8.55SPCh. 8 - Propose mechanisms consistent with the following...Ch. 8 - Prob. 8.57SPCh. 8 - Prob. 8.58SPCh. 8 - Draw a reaction-energy diagram for the propagation...Ch. 8 - Prob. 8.60SPCh. 8 - Prob. 8.61SPCh. 8 - Prob. 8.62SPCh. 8 - Prob. 8.63SPCh. 8 - Prob. 8.64SPCh. 8 - Prob. 8.65SPCh. 8 - Prob. 8.66SPCh. 8 - Prob. 8.67SPCh. 8 - Prob. 8.68SPCh. 8 - Prob. 8.69SPCh. 8 - Prob. 8.70SPCh. 8 - Prob. 8.71SPCh. 8 - Prob. 8.72SPCh. 8 - Prob. 8.73SPCh. 8 - Prob. 8.74SPCh. 8 - Prob. 8.75SPCh. 8 - Prob. 8.76SPCh. 8 - Prob. 8.77SPCh. 8 - Prob. 8.78SPCh. 8 - Prob. 8.79SP
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