Organic Chemistry-With Access and Study Guide / Solutions Manual
Organic Chemistry-With Access and Study Guide / Solutions Manual
7th Edition
ISBN: 9780321913364
Author: Bruice
Publisher: PEARSON
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Question
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Chapter 16.1, Problem 4P

a)

Interpretation Introduction

Interpretation:

The structure of phenyl acetate has to be drawn.

Concept Introduction:

Nomenclature of carboxylate (ester): Carboxylate (deprotonated form of carboxylic acid) is named by replacing the terminal ‘oic acid’ of the name with ‘oate’.  In common nomenclature, the position of a substituent is designated by a lowercase Greek letter, and the carbonyl carbon is not given a designation.  Thus, the carbon adjacent to the carbonyl carbon is the alpha-carbon, the carbon adjacent to the alpha-carbon is the beta-carbon, and so on.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  1

b)

Interpretation Introduction

Interpretation:

The structure of γ caprolactam has to be drawn.

Concept Introduction:

Nomenclature of Lactam: Cyclic amides are called lactam. In systematic name, ‘2-azacycloalkanones’ (‘aza’- indicates the nitrogen atom). For, common name, the length of the carbon chain is indicated by the common name of the carboxylic acid, and a Greek letter specifies the carbon to which the nitrogen is attached. 6-membered ring lactams are δ lactams (the carbonyl Nitrogen is on δ carbon, 5-membered ring lactams are γ lactams, and 4-membered ring lactams are β lactams.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  2

c)

Interpretation Introduction

Interpretation:

The structure of N-benzylethanamide has to be drawn.

Concept Introduction:

Nomenclature of Amides: Amides are named by replacing ‘oic acid’, ‘ic’ acid, or ‘ylic’ acid of the acid name with ‘amide’.  If a substituent is bonded to the nitrogen, the name of the substituent is stated first (if more, stated in alphabetical order) followed by the name of the amide.  The name of each substituent is preceded by N to indicate that the substituent is bonded to a nitrogen.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  3

d)

Interpretation Introduction

Interpretation:

The structure of γ- methylcaproic acid has to be drawn.

Concept Introduction:

Nomenclature of carboxylic acid: Carboxylic acid is named by replacing the terminal ‘e’ of the alkane or alkene name with ‘oic acid’. In common nomenclature, the position of a substituent is designated by a lowercase Greek letter, and the carbonyl carbon is not given a designation. Thus, the carbon adjacent to the carbonyl carbon is the alpha-carbon, the carbon adjacent to the alpha-carbon is the beta-carbon, and so on.

Carboxylic acids in which a carboxyl group is attached to a ring are named by adding ‘carboxylic acid’ to the name of the cyclic compound.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  4

e)

Interpretation Introduction

Interpretation:

The structure of ethyl 2-chloropentanoate has to be drawn.

Concept Introduction:

Nomenclature of carboxylate (ester): Carboxylate (deprotonated form of carboxylic acid) is named by replacing the terminal ‘oic acid’ of the name with ‘oate’. In common nomenclature, the position of a substituent is designated by a lowercase Greek letter, and the carbonyl carbon is not given a designation. Thus, the carbon adjacent to the carbonyl carbon is the alpha-carbon, the carbon adjacent to the alpha-carbon is the beta-carbon, and so on.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  5

f)

Interpretation Introduction

Interpretation:

The structure of β- bromobutyramide has to be drawn.

Concept Introduction:

Nomenclature of Amides: Amides are named by replacing ‘oic acid’, ‘ic’ acid, or ‘ylic’ acid of the acid name with ‘amide’. If a substituent is bonded to the nitrogen, the name of the substituent is stated first (if more, stated in alphabetical order) followed by the name of the amide. The name of each substituent is preceded by a N to indicate that the substituent is bonded to a nitrogen.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  6

g)

Interpretation Introduction

Interpretation:

The structure of cyclohexanecarbonyl chloride has to be drawn.

Concept Introduction:

Nomenclature of Acyl chlorides: Acyl chlorides are named by replacing ‘ic acid’ of the acid name with ‘yl chloride’. For cyclic acids, that end with ‘carboxylic acid’ is replaced with ‘carbonyl chloride’.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  7

h)

Interpretation Introduction

Interpretation:

The structure of α chlorovaleric acid has to be drawn.

Concept Introduction:

Nomenclature of carboxylic acid: Carboxylic acid is named by replacing the terminal ‘e’ of the alkane or alkene name with ‘oic acid’. In common nomenclature, the position of a substituent is designated by a lowercase Greek letter, and the carbonyl carbon is not given a designation. Thus, the carbon adjacent to the carbonyl carbon is the alpha-carbon, the carbon adjacent to the alpha-carbon is the beta-carbon, and so on.

Carboxylic acids in which a carboxyl group is attached to a ring are named by adding ‘carboxylic acid’ to the name of the cyclic compound.

Organic Chemistry-With Access and Study Guide / Solutions Manual, Chapter 16.1, Problem 4P , additional homework tip  8

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Chapter 16 Solutions

Organic Chemistry-With Access and Study Guide / Solutions Manual

Ch. 16.5 - a. What is the product of the reaction of acetyl...Ch. 16.6 - a. Which compound has the stretching vibration for...Ch. 16.6 - Using the pKa values listed in Table 15.1, predict...Ch. 16.6 - Is the following statement true or false? If the...Ch. 16.7 - What is the product of an acyl substitution...Ch. 16.8 - PROBLEM 16 Starting with acetyl chloride, what...Ch. 16.8 - Prob. 18PCh. 16.9 - We saw that it is necessary to use excess amine in...Ch. 16.9 - Prob. 20PCh. 16.9 - a. state three factors that cause the uncatalyzed...Ch. 16.10 - Prob. 23PCh. 16.10 - Using the mechanism for the acid-catalyzed...Ch. 16.10 - Prob. 25PCh. 16.10 - Prob. 27PCh. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.10 - Write the mechanism for the acid-catalyzed...Ch. 16.11 - Prob. 30PCh. 16.12 - Prob. 31PCh. 16.12 - Prob. 32PCh. 16.13 - Prob. 34PCh. 16.13 - Which has a higher melting point, glyceryl...Ch. 16.13 - Draw the structure of an optically inactive fat...Ch. 16.13 - Draw the structure of an optically active fat...Ch. 16.14 - Show how each of the following esters could he...Ch. 16.14 - Prob. 39PCh. 16.15 - Prob. 40PCh. 16.15 - Which of the following reactions leads to the...Ch. 16.16 - Prob. 42PCh. 16.16 - Prob. 43PCh. 16.18 - Prob. 44PCh. 16.18 - Prob. 45PCh. 16.19 - Prob. 46PCh. 16.19 - Which alkyl halides from the carboxylic acids...Ch. 16.20 - Prob. 49PCh. 16.20 - Prob. 50PCh. 16.20 - Prob. 51PCh. 16.21 - Prob. 52PCh. 16.21 - Prob. 53PCh. 16.22 - How could you synthesize the following compounds...Ch. 16 - Prob. 55PCh. 16 - Name the following:Ch. 16 - Prob. 57PCh. 16 - What compound are obtained from the fallowing...Ch. 16 - a. Rank the following esters in order of...Ch. 16 - Because bromocyclohexane is a secondary alkyl...Ch. 16 - a. Which compound would you expect to have a...Ch. 16 - How could you use 1H NMR spectroscopy to...Ch. 16 - Prob. 63PCh. 16 - a. When a carboxylic acid is dissolved in...Ch. 16 - Rank the following compounds in order of...Ch. 16 - Prob. 66PCh. 16 - Prob. 67PCh. 16 - Prob. 68PCh. 16 - A compound with molecular formula C5H10O2 gives...Ch. 16 - Prob. 70PCh. 16 - Prob. 71PCh. 16 - Prob. 72PCh. 16 - Two products, A and B, are obtained from the...Ch. 16 - Prob. 74PCh. 16 - Prob. 75PCh. 16 - Prob. 76PCh. 16 - Prob. 77PCh. 16 - When treated with an equivalent of methanol,...Ch. 16 - a. Identify the two products obtained from the...Ch. 16 - Prob. 80PCh. 16 - Identity the major and minor products of the...Ch. 16 - Prob. 82PCh. 16 - When a compound with molecular formula C11H14O2...Ch. 16 - Prob. 84PCh. 16 - Prob. 85PCh. 16 - The 1H NMR spectra for two esters with molecular...Ch. 16 - Show how the following compounds could be prepared...Ch. 16 - Prob. 88PCh. 16 - Prob. 89PCh. 16 - Prob. 90PCh. 16 - The intermediate shown here is formed during the...Ch. 16 - Prob. 92PCh. 16 - Propose a mechanism that accounts for the...Ch. 16 - Catalytic antibodies catalyze a reaction by...Ch. 16 - Prob. 95P
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