Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
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Chapter 11.3, Problem 11.3P

(a)

Interpretation Introduction

To determine: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone; and the number of bonds to oxygen that each atom has before and after the oxidation.

Interpretation: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone; and the number of bonds to oxygen that each atom has before and after the oxidation is to be stated.

Concept introduction: Chromic acid is an oxidizing agent in which chromium acts as a multivalent atom. The formation of active species of chromic acid occurs by going through higher oxidation state before the oxidation to a lower oxidation state after the oxidation of alcohol.

(b)

Interpretation Introduction

To determine: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone; and the number of bonds to oxygen that each atom has before and after the oxidation.

Interpretation: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone and the number of bonds to oxygen does each atom before and after the oxidation is to be stated.

Concept introduction: Sodium hypochlorite is an oxidizing agent in which chlorine acts as a multivalent atom. The formation of active species of sodium hypochlorite occurs by going through higher oxidation state before the oxidation to a lower oxidation state after the oxidation of alcohol.

(c)

Interpretation Introduction

To determine: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone; and the number of bonds to oxygen that each atom has before and after the oxidation.

Interpretation: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone and the number of bonds to oxygen does each atom before and after the oxidation is to be stated.

Concept introduction: Sulphur in the Swern oxidation acts as a multivalent atom. The Swern oxidation comprises use of DMSO reagent. The formation of active species (sulfur) in Swern reagent occurs by going through higher oxidation state before the oxidation to a lower oxidation state after the oxidation of alcohol.

(d)

Interpretation Introduction

To determine: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone; and the number of bonds to oxygen that each has atom before and after the oxidation.

Interpretation: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone; and the number of bonds to oxygen that each atom has before and after the oxidation is to be stated.

Concept introduction: Iodine in the DMP reagent acts as a multivalent atom. The formation of active species in the DMP reagent occurs by going through higher oxidation state before the oxidation to a lower oxidation state after the oxidation of alcohol.

(e)

Interpretation Introduction

To determine: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone, and the number of bonds to oxygen that each atom has before and after the oxidation.

Interpretation: The Lewis structure of the given atom, before and after the oxidation of an alcohol to an aldehyde or ketone and the number of bonds to oxygen that each atom has, before and after the oxidation is to be stated.

Concept introduction: The carbinol C in the alcohol (oxidized) acts as a multivalent atom. The formation of active species in the carbinol C occurs by going through higher oxidation state before the oxidation to a lower oxidation state after the oxidation of alcohol.

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We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as theiractive species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, beforeand after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygendoes each atom have before and after the oxidation?(a) the Cr in chromic acid (b) the Cl in sodium hypochlorite(c) the S in the Swern oxidation (d) the I in the DMP reagent(e) the carbinol C in the alcohol that is oxidized
WHich statement is true? Statement 1: The ignition test for hydrocarbons is based on the sootiness of the flames they produce when burned. Unsaturated compounds produce black powdery or flaky substances consisting largely of amorphous carbon which is due to the incomplete combustion of organic matter. Statement 2: In the bromine test for unsaturation, the disappearance of the orange or red-brown color of bromine is due to the electrophilic addition reaction of bromine with the pi bond.
A student left some alkyl halides (RC1 and RBr) in an open container for several minutes. What happened to the composition of the halide mixture during that time? Assume that some liquid remains in the container.

Chapter 11 Solutions

Organic Chemistry (9th Edition)

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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