General, Organic, and Biochemistry
General, Organic, and Biochemistry
9th Edition
ISBN: 9780078021541
Author: Katherine J Denniston, Joseph J Topping, Dr Danae Quirk Dorr
Publisher: McGraw-Hill Education
Question
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Chapter 14, Problem 14.96QP

(a)

Interpretation Introduction

Interpretation:

The equation representing the reaction of butanoic anhydride with propanol has to be written and the IUPAC name of the products has to be provided.

Concept Introduction:

Acid anhydrides are compounds with the formula,

General, Organic, and Biochemistry, Chapter 14, Problem 14.96QP , additional homework tip  1

Acid anhydrides react with an alcohol to produce an ester and a carboxylic acid.  This is an example of an acyl group transfer reaction.

The general reaction of acyl group transfer reaction between an alcohol and an acid anhydride is written as,

General, Organic, and Biochemistry, Chapter 14, Problem 14.96QP , additional homework tip  2

The acyl group of the acid anhydride is transferred to the oxygen of the alcohol and the products of esters are produced.  The carboxylic acid product is omitted.

Nomenclature of Esters

The simplest method to name an ester starts by identifying the carboxylic acid and alcohol.

General, Organic, and Biochemistry, Chapter 14, Problem 14.96QP , additional homework tip  3

The first part of the name of an ester is the alkyl or aryl group of the alcohol

  • The name of the parent alcohol is identified and the name of the corresponding alkyl or aryl group is written.

The second part of the name is derived from the carboxylic acid

  • The name of the parent carboxylic acid is identified and the suffix -ic is replaced with –ate.

(b)

Interpretation Introduction

Interpretation:

The equation representing the reaction of pentanoic anhydride with propanol has to be written and the IUPAC name of the products has to be provided.

Concept Introduction:

Refer to part (a).

(c)

Interpretation Introduction

Interpretation:

The equation representing the reaction of methanoic anhydride with propanol has to be written and the IUPAC name of the products has to be provided.

Concept Introduction:

Refer to part (a).

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Part II. two unbranched ketone have molecular formulla (C8H100). El-ms showed that both of them have a molecular ion peak at m/2 =128. However ketone (A) has a fragment peak at m/2 = 99 and 72 while ketone (B) snowed a fragment peak at m/2 = 113 and 58. 9) Propose the most plausible structures for both ketones b) Explain how you arrived at your conclusion by drawing the Structures of the distinguishing fragments for each ketone, including their fragmentation mechanisms.
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Chapter 14 Solutions

General, Organic, and Biochemistry

Ch. 14.1 - Prob. 14.5PPCh. 14.1 - Prob. 14.6PPCh. 14.2 - Prob. 14.7PPCh. 14.2 - Prob. 14.8PPCh. 14.2 - Prob. 14.9PPCh. 14.2 - Prob. 14.7QCh. 14.2 - Prob. 14.8QCh. 14.3 - Prob. 14.10PPCh. 14.3 - Write the common and IUPAC names for each of the...Ch. 14.3 - Prob. 14.9QCh. 14.3 - Prob. 14.10QCh. 14 - Prob. 14.11QPCh. 14 - Prob. 14.12QPCh. 14 - Prob. 14.13QPCh. 14 - Prob. 14.14QPCh. 14 - Prob. 14.15QPCh. 14 - Prob. 14.16QPCh. 14 - Prob. 14.17QPCh. 14 - Which member in each of the following pairs is...Ch. 14 - Prob. 14.19QPCh. 14 - Prob. 14.20QPCh. 14 - Prob. 14.21QPCh. 14 - Prob. 14.22QPCh. 14 - Prob. 14.23QPCh. 14 - Prob. 14.24QPCh. 14 - Prob. 14.25QPCh. 14 - Prob. 14.26QPCh. 14 - Prob. 14.27QPCh. 14 - Prob. 14.28QPCh. 14 - Prob. 14.29QPCh. 14 - Prob. 14.30QPCh. 14 - Prob. 14.31QPCh. 14 - Prob. 14.32QPCh. 14 - Prob. 14.33QPCh. 14 - Prob. 14.34QPCh. 14 - Prob. 14.35QPCh. 14 - Prob. 14.36QPCh. 14 - Prob. 14.37QPCh. 14 - Prob. 14.38QPCh. 14 - Prob. 14.39QPCh. 14 - Prob. 14.40QPCh. 14 - Prob. 14.41QPCh. 14 - Prob. 14.42QPCh. 14 - Prob. 14.43QPCh. 14 - Prob. 14.44QPCh. 14 - Prob. 14.45QPCh. 14 - Prob. 14.46QPCh. 14 - Prob. 14.47QPCh. 14 - Prob. 14.48QPCh. 14 - Write an equation representing the oxidation of...Ch. 14 - Prob. 14.50QPCh. 14 - Prob. 14.51QPCh. 14 - Prob. 14.52QPCh. 14 - Prob. 14.54QPCh. 14 - Write an equation representing the neutralization...Ch. 14 - Prob. 14.56QPCh. 14 - Prob. 14.57QPCh. 14 - Prob. 14.58QPCh. 14 - Prob. 14.59QPCh. 14 - Prob. 14.60QPCh. 14 - Prob. 14.61QPCh. 14 - Prob. 14.62QPCh. 14 - Prob. 14.63QPCh. 14 - Draw condensed formulas for each of the following...Ch. 14 - Prob. 14.65QPCh. 14 - Prob. 14.66QPCh. 14 - Prob. 14.67QPCh. 14 - Prob. 14.68QPCh. 14 - Prob. 14.69QPCh. 14 - Prob. 14.70QPCh. 14 - Prob. 14.71QPCh. 14 - Prob. 14.72QPCh. 14 - Prob. 14.73QPCh. 14 - Prob. 14.74QPCh. 14 - Prob. 14.75QPCh. 14 - Prob. 14.76QPCh. 14 - Prob. 14.77QPCh. 14 - Prob. 14.78QPCh. 14 - Prob. 14.79QPCh. 14 - Prob. 14.80QPCh. 14 - Prob. 14.81QPCh. 14 - Prob. 14.82QPCh. 14 - Prob. 14.83QPCh. 14 - Prob. 14.84QPCh. 14 - Prob. 14.85QPCh. 14 - Prob. 14.86QPCh. 14 - Prob. 14.87QPCh. 14 - Prob. 14.88QPCh. 14 - Prob. 14.89QPCh. 14 - Prob. 14.90QPCh. 14 - Prob. 14.91QPCh. 14 - Prob. 14.92QPCh. 14 - Prob. 14.93QPCh. 14 - Prob. 14.94QPCh. 14 - Prob. 14.95QPCh. 14 - Prob. 14.96QPCh. 14 - Prob. 14.97QPCh. 14 - What is meant by a phosphoanhydride bond? Ch. 14 - Prob. 14.99QPCh. 14 - Prob. 14.100QPCh. 14 - Prob. 14.101QPCh. 14 - Prob. 14.102QPCh. 14 - Prob. 14.103QPCh. 14 - Triglycerides are the major lipid storage form in...Ch. 14 - Prob. 3CPCh. 14 - Acetyl coenzyme A (acetyl CoA) can serve as a...Ch. 14 - Prob. 5CP
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