Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter A, Problem A.44P
Interpretation Introduction

(a)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  1

Explanation of Solution

The given IUPAC name is 2, 4-dicyclopropyl-2-ethoxyhexane.

The root name ‘hexane’ indicates the parent chain is of six carbon atoms.

Thus, the chain is numbered as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  2

In the IUPAC name 2, 4-dicyclopropyl indicates that the substituent cyclopropyl is attached to C-2 and C-4 of parent chain and the 2-ethoxy indicates the substituent ethoxy is attached to C-2 of parent chain.

Hence, the structure of 2, 4-dicyclopropyl-2-ethoxyhexane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  3

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

Interpretation Introduction

(b)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for 1, 2-dichloro-1-(2-methylpropyl)-4-nitrocyclohexane is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  4

Explanation of Solution

The given IUPAC name is 1, 2-dichloro-1-(2-methylpropyl)-4-nitrocyclohexane.

The root name cyclohexane indicates the parent is a ring of six carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  5

1, 2-dichloro indicates two chlorine atoms bonded to C-1 and C-2.

1-(2-methylpropyl) indicates, to the propyl parent chain, a methyl group is attached to the second carbon atom and this whole substituent is attached to the C-1 atom of the cyclohexane ring.

4-nitro indicates the nitro group attached to C-4 of the cyclohexane ring.

Hence, the structure of 1, 2-dichloro-1-(2-methylpropyl)-4-nitrocyclohexane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  6

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

Interpretation Introduction

(c)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  7

Explanation of Solution

The given IUPAC name is 1, 3-dicyclopentyl-1, 2, 3, 4-tetramethoxycyclooctane.

The root name cyclooctane indicates the parent is a ring of eight carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  8

1, 3-dicyclopentyl indicates the presence of two cyclopentyl groups attached to C-1 and C-3 carbon atom of the cyclooctane.

1, 2, 3, 4-tetramethoxy indicates four methoxy groups bonded to C-1, C-2, C-3 and C-4 carbon atoms of cyclooctane.

Hence, the structure of 1, 3-dicyclopentyl-1, 2, 3, 4-tetramethoxycyclooctane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  9

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

Interpretation Introduction

(d)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  10

Explanation of Solution

The given IUPAC name is 1-cyclobutyl-4-(1, 1-dimethylethyl)-2, 4-dinitrononane.

The root name nonane indicates the parent is a chain of nine carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  11

1-cyclobutyl indicates the cyclobutyl group bonded to C-1 carbon atom of nonane.

4-(1, 1-dimethylethyl) indicates the 1, 1-dimethylethyl group i.e. tert-butyl group bonded to C-4 carbon atom of nonane.

2, 4-dinitro indicates the presence of two nitro groups respectively at C-2 and C-4 carbon atoms of nonane.

Hence, the structure of 1-cyclobutyl-4-(1, 1-dimethylethyl)-2, 4-dinitrononane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  12

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

Interpretation Introduction

(e)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  13

Explanation of Solution

The given IUPAC name is 1-(1, 1-dimethylbutyl)-2-ethoxy-1, 2, 3-trinitrocyclobutane.

The root name cyclobutane indicates the parent is a ring of four carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  14

1-(1, 1-dimethylbutyl) indicates the 1, 1-dimethylbutyl group bonded to C-1 carbon atom of cyclobutane ring.

2-ethoxy indicates the ethoxy group bonded to C-2 and 1, 2, 3-trinitro indicates the presence of three nitro groups respectively at C-1, C-2 and C-3.

Hence, the structure of 1-(1, 1-dimethylbutyl)-2-ethoxy-1, 2, 3-trinitrocyclobutane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  15

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituents.

Interpretation Introduction

(f)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  16

Explanation of Solution

The given IUPAC name is 1, 2, 4-tricyclopropyl-1-(2, 2-dichloropentyl)cyclohexane.

The root name cyclohexane indicates the parent is a ring of six carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  17

1, 2, 4-tricyclopropyl indicates there are three cyclopropyl groups bonded to C-1, C-2 and C-4.

1-(2, 2-dichloropentyl) indicates the substituent 2, 2-dichloropentyl is bonded to ring at C-1.

Hence, the structure of 1, 2, 4-tricyclopropyl-1-(2, 2-dichloropentyl)cyclohexane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  18

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

Interpretation Introduction

(g)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  19

Explanation of Solution

The given IUPAC name is 4-(2-chloro-1-methoxyethyl)-1, 1-dinitroheptane.

The root name heptane indicates the parent is a chain of seven carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  20

4-(2-chloro-1-methoxyethyl) indicates the substituent 2-chloro-1-methoxyethyl bonded to parent chain at C-4. The structure for the substituent 2-chloro-1-methoxyethyl is given below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  21

1, 1-dinitro indicates the two nitro groups bonded to parent chain at C-1 and C-2.

Hence, the structure of 4-(2-chloro-1-methoxyethyl)-1, 1-dinitroheptane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  22

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

Interpretation Introduction

(h)

Interpretation:

The structure for the given IUPAC name is to be drawn.

Concept introduction:

The root name in the IUPAC name is the parent alkane. The longest continuous carbon chain must be drawn from the root name and numbered. The substituents are attached to the desired carbon number according to locator numbers given in the IUPAC name. The prefix indicates the number of identical substituents in the molecule.

Expert Solution
Check Mark

Answer to Problem A.44P

The structure for the given IUPAC name is as follows:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  23

Explanation of Solution

The given IUPAC name is 3, 3, 4-trichloro-1-cyclohexoxy-4-(1, 1-dichloroethyl)decane.

The root name decane indicates the parent is a chain of ten carbon atoms.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  24

3, 3, 4-trichloro indicates the presence of three chlorine atoms, two of them are bonded to C-3 and one is bonded to C-4.

1-cyclohexoxy indicates the cyclohexoxy group bonded to C-1 and 4-(1, 1-dichloroethyl) indicates the substituent 1, 1-dichloroethyl bonded to chain at C-4.

Hence, the structure of 3, 3, 4-trichloro-1-cyclohexoxy-4-(1, 1-dichloroethyl)decane is drawn below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter A, Problem A.44P , additional homework tip  25

Conclusion

The structure for the given molecules is drawn from the root name, prefix and locator of substituent.

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Write a complete chemical equation showing reactants, products, and catalysts needed(if any) for the following reaction and (2) Draw and name the organic compound found inevery reaction.(Use condensed structural formula) (A) Reaction of cis-3,3-Dimethyl-4-propylocta-1,5-diene with two mole of HBr(B) Reaction of trans-1-Bromo-3-chlorocyclopentane with potassium hydroxide(C) Formation of Gilman reagent using isopropyl bromide
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