ORGANIC CHEMISTRY,VOL.1 >CUSTOM<
ORGANIC CHEMISTRY,VOL.1 >CUSTOM<
10th Edition
ISBN: 9781260020724
Author: Carey
Publisher: MCG CUSTOM
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Textbook Question
Chapter 3, Problem 20P

Give the IUPAC names of each of the following:

Chapter 3, Problem 20P, Give the IUPAC names of each of the following: (a) (b) (c) , example  1

Chapter 3, Problem 20P, Give the IUPAC names of each of the following: (a) (b) (c) , example  2

Chapter 3, Problem 20P, Give the IUPAC names of each of the following: (a) (b) (c) , example  3

(a) (b) (c)

Expert Solution & Answer
Check Mark
Interpretation Introduction

Interpretation:

IUPAC names of the given structures are to be determined.

Concept introduction:

When writing the IUPAC name, the longest continuous carbon chain is first determined. The parent chain is numbered such that the substituents get the lowest numbers.

The location of each substituent group is designated by an appropriate number and name. Prefixes are used if more than one substituents of the same type are present. The substituents are written in alphabetical order.

A cyclic ring hydrocarbon is designated by the prefix cyclo- which appears in front of the base name.

Answer to Problem 20P

Solution:

2,4-dimethylpentane

2,2,4-trimethylhexane

trans -1- ethyl - 4 - isopropylcyclononane

Explanation of Solution

(a)

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  1

In the given Newman projection, the carbon atom at the front is a CH3 group. The carbon atom at the back is attached to a CH3 group, H, and the (CH3)2CHCH2 group. From this, the skeletal structure is drawn as shown below:

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  2

In this structure, the longest chain contains five carbon atoms, so the parent alkane is pentane. There are two methyl groups attached to this parent chain. The pentane chain is numbered such that these methyl groups get the lowest numbers.

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  3

The two methyl groups are attached to the carbon atoms C2 and C4. The prefix “di” is used to show the presence of two methyl groups. There are no chiral carbon atoms in this structure. Therefore, the IUPAC name of the compound is 2,4-dimethylpentane.

(b)ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  4

The given sawhorse projection is converted to a skeletal structure as follows:

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  5

In this structure, the longest chain contains six carbon atoms, so the parent alkane is hexane. There are three methyl groups attached to the hexane chain. The chain is numbered such that the carbon atoms attached to these three methyl groups get the lowest numbers.

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  6

Two methyl groups are attached to C2 while one methyl group is attached to C4. The prefix “tri” is used to show the presence of three methyl groups. The IUPAC name of the compound is 2,2,4-trimethylhexane.

(c)ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  7

In the given structure, there are nine carbon atoms in the ring. So the name of parent alkane is cyclononane. The ring is numbered such that the two substituents get the lowest numbers.

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<, Chapter 3, Problem 20P , additional homework tip  8

There is an ethyl group and an isopropyl group attached to the cyclononane ring. These two groups are trans to each other. Hence the ring is numbered such that the ethyl group gets the lower number since it comes first alphabetically. The IUPAC name of the compound is trans -1- ethyl - 4 - isopropylcyclononane.

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Chapter 3 Solutions

ORGANIC CHEMISTRY,VOL.1 >CUSTOM<

Ch. 3.11 - Prob. 11PCh. 3.12 - Based on what you know about disubstituted...Ch. 3.12 - Write structural formulas for the most stable...Ch. 3.14 - Cubane (C4H8) is the common name of the polycyclic...Ch. 3.14 - Prob. 15PCh. 3.14 - Prob. 16PCh. 3.14 - Prob. 17PCh. 3.14 - Prob. 18PCh. 3.15 - Prob. 19PCh. 3 - Give the IUPAC names of each of the following: (a)...Ch. 3 - Draw Newman projections for the gauche and...Ch. 3 - Identify all atoms that are (a) anti and (b)...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Prob. 25PCh. 3 - Prob. 26PCh. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Oxidation of 4-tert-butylthiane proceeds according...Ch. 3 - The following are representations of two forms of...Ch. 3 - Draw (a) a Newman projection of the most stable...Ch. 3 - Write a structural formula for the most stable...Ch. 3 - Sight down the C-2-C-3 bond, and draw Newman...Ch. 3 - Prob. 34PCh. 3 - Sketch an approximate potential energy diagram for...Ch. 3 - Prob. 36PCh. 3 - Even though the methyl group occupies an...Ch. 3 - Which do you expect to be the more stable...Ch. 3 - Arrange the trimethylcyclohexane isomers shown in...Ch. 3 - Identify the more stable stereoisomer in each of...Ch. 3 - One stereoisomer of 1,1,3,5-tetramethylcyclohexane...Ch. 3 - One of the following two stereoisomers is...Ch. 3 - In each of the following groups of compounds,...Ch. 3 - The heats of combustion of the more and less...Ch. 3 - The measured dipole moment of ClCH2CH2Cl is 1.12D....Ch. 3 - Prob. 46PCh. 3 - Prob. 47PCh. 3 - Prob. 48DSPCh. 3 - Prob. 49DSPCh. 3 - Prob. 50DSPCh. 3 - Prob. 51DSPCh. 3 - Prob. 52DSPCh. 3 - Prob. 53DSP
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