GENERAL,ORGANIC,+BIOCHEMISTRY
GENERAL,ORGANIC,+BIOCHEMISTRY
10th Edition
ISBN: 9781260148954
Author: Denniston
Publisher: RENT MCG
Question
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Chapter 11, Problem 11.41QP

(a)

Interpretation Introduction

Interpretation:

Condensed formula for 2-methyl-2-hexene has to be drawn.

Concept Introduction:

Organic compounds can be drawn from its IUPAC name.  Initially, the parent chain is identified from the IUPAC name.  After that the carbon chain is drawn with carbon atoms alone.  Next step is to add the substituents in the respective positions as indicated in the IUPAC name.  Remaining valency of carbon atom is satisfied by adding correct number of hydrogen atoms.

Condensed structural formula is a simplified form of representation of a molecule.  This gives the information about all the atoms present in molecule and the atoms are placed in sequential order which gives information about which atom is bonded to other atom.

(a)

Expert Solution
Check Mark

Explanation of Solution

Given IUPAC name is 2-methyl-2-hexene.  From this the parent alkane is identified as hexane.  Hexane contains six carbon atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  1

Numbering of each carbon has to be done as shown,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  2

From the name it is understood that a double bond is present between carbon-2 and carbon-3.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  3

Substituent that is present is a methyl group on carbon-2.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  4

Remaining valency of carbon atom has to be balanced by adding hydrogen atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  5

Condensed formula can be obtained as shown below,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  6

Condensed formula for 2-methyl-2-hexene is drawn as shown.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  7

(b)

Interpretation Introduction

Interpretation:

Condensed formula for trans-3-heptene has to be drawn.

Concept Introduction:

Refer part (a).

(b)

Expert Solution
Check Mark

Explanation of Solution

Given IUPAC name is trans-3-heptene.  From this the parent alkane is identified as heptane.  Heptane contains seven carbon atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  8

Numbering of each carbon has to be done as shown,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  9

From the name it is understood that a double bond is present between carbon-3 and carbon-4.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  10

As the stereo information is given as trans-, the hydrogen atom that is bonded to the carbon atoms across the double bond has to be in opposite side.  Remaining valency of carbon atom has to be balanced by adding hydrogen atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  11

Condensed formula can be obtained as shown below,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  12

Condensed formula for trans-3-heptene is drawn as shown.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  13

(c)

Interpretation Introduction

Interpretation:

Condensed formula for cis-1-chloro-2-pentene has to be drawn.

Concept Introduction:

Refer part (a).

(c)

Expert Solution
Check Mark

Explanation of Solution

Given IUPAC name is cis-1-chloro-2-pentene.  From this the parent alkane is identified as pentane.  Pentane contains five carbon atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  14

Numbering of each carbon has to be done as shown,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  15

From the name it is understood that a double bond is present between carbon-2 and carbon-3.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  16

As the stereo information is given as cis-, the hydrogen atom that is bonded to the carbon atoms across the double bond has to be in same side.  Subsituents present in the given name is a chlorine atom in on carbon-1.  Remaining valency of carbon atom has to be balanced by adding hydrogen atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  17

Condensed formula can be obtained as shown below,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  18

Condensed formula for cis-1-chloro-2-pentene is drawn as shown.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  19

(d)

Interpretation Introduction

Interpretation:

Condensed formula for cis-2-chloro-2-methyl-3-heptene has to be drawn.

Concept Introduction:

Refer part (a).

(d)

Expert Solution
Check Mark

Explanation of Solution

Given IUPAC name is cis-2-chloro-2-methyl-3-heptene.  From this the parent alkane is identified as heptane.  Heptane contains seven carbon atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  20

Numbering of each carbon has to be done as shown,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  21

From the name it is understood that a double bond is present between carbon-3 and carbon-4.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  22

As the stereo information is given as cis-, the hydrogen atom that is bonded to the carbon atoms across the double bond has to be in same side.  Substituents present in the given name are a chlorine atom in on carbon-2 and methyl group on carbon-2.  Remaining valency of carbon atom has to be balanced by adding hydrogen atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  23

Condensed formula can be obtained as shown below,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  24

Condensed formula for cis-2-chloro-2-methyl-3-heptene is drawn as shown.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  25

(e)

Interpretation Introduction

Interpretation:

Condensed formula for trans-5-bromo-2,6-dimethyl-3-octene has to be drawn.

Concept Introduction:

Refer part (a).

(e)

Expert Solution
Check Mark

Explanation of Solution

Given IUPAC name is trans-5-bromo-2,6-dimethyl-3-octene.  From this the parent alkane is identified as octane.  Octane contains eight carbon atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  26

Numbering of each carbon has to be done as shown,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  27

From the name it is understood that a double bond is present between carbon-3 and carbon-4.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  28

As the stereo information is given as trans-, the hydrogen atom that is bonded to the carbon atoms across the double bond has to be in opposite side.  Substituents present in the given name are a bromine atom in on carbon-5, a methyl group on carbon-2, and a methyl group on carbon-6.  Remaining valency of carbon atom has to be balanced by adding hydrogen atoms.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  29

Condensed formula can be obtained as shown below,

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  30

Condensed formula for trans-5-bromo-2,6-dimethyl-3-octene is drawn as shown.

GENERAL,ORGANIC,+BIOCHEMISTRY, Chapter 11, Problem 11.41QP , additional homework tip  31

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Chapter 11 Solutions

GENERAL,ORGANIC,+BIOCHEMISTRY

Ch. 11.3 - Draw each of the cis-trans isomers in Question...Ch. 11.3 - Prob. 11.7QCh. 11.3 - Prob. 11.8QCh. 11.5 - Prob. 11.6PPCh. 11.5 - Prob. 11.7PPCh. 11.5 - Prob. 11.9QCh. 11.5 - Write balanced equations for the hydrogenation of...Ch. 11.5 - Prob. 11.11QCh. 11.5 - Prob. 11.12QCh. 11.5 - Prob. 11.8PPCh. 11.5 - Prob. 11.13QCh. 11.5 - Prob. 11.14QCh. 11.5 - Prob. 11.15QCh. 11.5 - Prob. 11.16QCh. 11.5 - Prob. 11.9PPCh. 11.5 - Prob. 11.17QCh. 11.5 - Prob. 11.18QCh. 11.5 - Prob. 11.19QCh. 11.5 - Prob. 11.20QCh. 11.5 - Write a balanced equation for the hydrobromination...Ch. 11.6 - Name the following compounds using the IUPAC and...Ch. 11.6 - Prob. 11.21QCh. 11.6 - Prob. 11.22QCh. 11 - Prob. 11.23QPCh. 11 - Prob. 11.24QPCh. 11 - Prob. 11.25QPCh. 11 - Prob. 11.26QPCh. 11 - Prob. 11.27QPCh. 11 - Prob. 11.28QPCh. 11 - Prob. 11.29QPCh. 11 - Prob. 11.30QPCh. 11 - Prob. 11.31QPCh. 11 - Prob. 11.32QPCh. 11 - Prob. 11.33QPCh. 11 - Prob. 11.34QPCh. 11 - Prob. 11.35QPCh. 11 - Prob. 11.36QPCh. 11 - Prob. 11.37QPCh. 11 - Prob. 11.38QPCh. 11 - Prob. 11.39QPCh. 11 - Prob. 11.40QPCh. 11 - Prob. 11.41QPCh. 11 - Prob. 11.42QPCh. 11 - Prob. 11.43QPCh. 11 - Prob. 11.44QPCh. 11 - Prob. 11.45QPCh. 11 - Prob. 11.46QPCh. 11 - Which of the following alkenes can exist as...Ch. 11 - Prob. 11.48QPCh. 11 - Prob. 11.49QPCh. 11 - Prob. 11.50QPCh. 11 - Prob. 11.51QPCh. 11 - Prob. 11.52QPCh. 11 - Prob. 11.53QPCh. 11 - Prob. 11.54QPCh. 11 - Prob. 11.55QPCh. 11 - Prob. 11.56QPCh. 11 - Prob. 11.57QPCh. 11 - Prob. 11.58QPCh. 11 - Prob. 11.59QPCh. 11 - Prob. 11.60QPCh. 11 - Prob. 11.61QPCh. 11 - Prob. 11.62QPCh. 11 - Prob. 11.63QPCh. 11 - Prob. 11.64QPCh. 11 - Prob. 11.65QPCh. 11 - Prob. 11.66QPCh. 11 - Prob. 11.67QPCh. 11 - Prob. 11.68QPCh. 11 - Prob. 11.69QPCh. 11 - Prob. 11.70QPCh. 11 - Prob. 11.71QPCh. 11 - Prob. 11.72QPCh. 11 - Prob. 11.73QPCh. 11 - Prob. 11.74QPCh. 11 - Prob. 11.75QPCh. 11 - Prob. 11.76QPCh. 11 - Prob. 11.77QPCh. 11 - Prob. 11.78QPCh. 11 - Prob. 11.79QPCh. 11 - Prob. 11.80QPCh. 11 - Prob. 11.81QPCh. 11 - Prob. 11.82QPCh. 11 - Prob. 11.83QPCh. 11 - Write an equation for the addition reaction that...Ch. 11 - Prob. 11.85QPCh. 11 - Draw the structure of each of the following...Ch. 11 - Prob. 11.87QPCh. 11 - Prob. 11.88QPCh. 11 - Prob. 11.89QPCh. 11 - Prob. 11.90QPCh. 11 - Prob. 11.91QPCh. 11 - Prob. 11.92QPCh. 11 - Draw each of the following compounds, using...Ch. 11 - Prob. 11.94QPCh. 11 - Prob. 11.95QPCh. 11 - Prob. 11.96QPCh. 11 - Prob. 11.97QPCh. 11 - Prob. 11.98QPCh. 11 - Prob. 11.99QPCh. 11 - Prob. 11.100QPCh. 11 - Prob. 11.101QPCh. 11 - Prob. 11.102QPCh. 11 - Prob. 11.103QPCh. 11 - What biological molecules contain purine rings? Ch. 11 - Prob. 1MCPCh. 11 - Prob. 3MCPCh. 11 - Prob. 5MCPCh. 11 - Prob. 6MCPCh. 11 - Prob. 7MCPCh. 11 - Prob. 8MCPCh. 11 - Prob. 9MCPCh. 11 - Prob. 10MCP
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