General, Organic, and Biological Chemistry - 4th edition
General, Organic, and Biological Chemistry - 4th edition
4th Edition
ISBN: 9781259883989
Author: by Janice Smith
Publisher: McGraw-Hill Education
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Chapter 13, Problem 95P

Answer the following questions about compound A, represent in the given ball-and-stick model.

Chapter 13, Problem 95P, Answer the following questions about compound A, represent in the given ball-and-stick model.

  1. Convert A to a condensed structure and give its IUPAC name.
  2. What product is formed when A is treated with H2 in the presence of metal catalyst?
  3. What product is formed when A is treated with H2O in the presence of H2SO4?
  4. What polymer is formed when A is polymerized?

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation:

Structure of the molecule A should be converted to a condensed structure and IUPAC name of the molecule should be given.

  General, Organic, and Biological Chemistry - 4th edition, Chapter 13, Problem 95P , additional homework tip  1 = ( C7H14 )

Concept Introduction:

Alkenes are hydrocarbon molecules that consist of a carbon-carbon double bond which has the general formula of CnH2n . The structure of a chemical compound is the arrangement of atoms and bonds in the space.

In alkene nomenclature, the longest C chain will be considered as the parent/ main C chain. At the end of the alkane suffix -ene is added. The longest chain which includes the carbon-carbon double bond will be considered as the main carbon chain. The numbering of the main C chain is starting from the first substituent by giving the lower number to that substituent and as well as the double bond should get the lower number. All the substituents should be numbered and named. Two or more identical substituents should be indicated by using appropriate prefixes as di-. Names of the substituents should be alphabetized. Each substituent should have a position number which is mentioned in the main C chain.

Answer to Problem 95P

Condensed structure −

  General, Organic, and Biological Chemistry - 4th edition, Chapter 13, Problem 95P , additional homework tip  2

IUPAC name −Heptene

Explanation of Solution

In alkenes, there is a carbon-carbon double bond and different groups are connected to the two carbons. In most of the alkenes; out of four binding positions of carbon-carbon double bond, two of them are bind with two hydrogen atoms and the other two binding positions bind with two different alkyl groups. In this molecule, carbon atoms are represented in black and hydrogen atoms are represented in white color. The structure of a chemical compound is the arrangement of atoms and bonds in the space.

Condensed structure −

  General, Organic, and Biological Chemistry - 4th edition, Chapter 13, Problem 95P , additional homework tip  3

In this molecule, the main carbon chain which contains the carbon-carbon double bond is a seven-membered chain and there are no substituents in this molecule. According to the numbering of the main chain double bond gets the lowest number and it is number 1. Hence, the IUPAC name of the molecule is heptene.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation:

The resulting product should be identified after reacting C7H14 with H2 in the presence of a metal catalyst.

Concept Introduction:

Alkenes are hydrocarbon molecules that contain a carbon-carbon double bond which has the general formula of CnH2n . Alkanes are hydrocarbon molecules which do not have any functional group.

Reaction of alkene with H2 in the presence of Pd will form saturated alkanes and the reaction is called as hydrogenation reaction.

Answer to Problem 95P

  CH3CH2CH2CH2CH2CH2CH3

Explanation of Solution

Unsaturated ( C7H14 ) alkene molecule react with H2 in the presence of Pd ( a metal) and form saturated alkanes. Bond between two H in the H2 , is broken and also a bond between two carbon-carbon double bond is broken, meanwhile new two bonds of CH are formed in the presence of Pd metallic catalyst, which reduce the activation energy of the reaction. Refer to the below reaction;

  CH2=CHCH2CH2CH2CH2CH3H2/PdCH3CH2CH2CH2CH2CH2CH3

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation:

The resulting product should be identified after reacting C7H14 with H2O and H2SO4.

Concept Introduction:

Alkenes are hydrocarbon molecules that consist a carbon-carbon double bond which has the general formula of CnH2n . Alcohols are the hydrocarbon molecules which contains OH group in the molecule.

Reaction of alkene with H2O and H2SO4 will form saturated alcohols and the reaction is called as hydration reaction.

Hydration reaction of alkenes follows the Markovnikov's rule.

Answer to Problem 95P

  CH3CHOHCH2CH2CH2CH2CH3

Explanation of Solution

Unsaturated ( C7H14 ) alkene molecule react with H2O and H2SO4 , form alcohols. One bond between a hydrogen atom and an oxygen atom in the H2O , is broken and also a one bond between two carbon-carbon bond is broken, meanwhile new two bonds of COH and CH are formed. Hydrogenation occurs only in the presence of a strong acid such as H2SO4 . Hydration reaction of alkenes follows the Markovnikov's rule. When addition of H2O molecule to an unsymmetrical alkene, H atom binds to the less substituted carbon atom is known as Markovnikov's rule. This molecule also falls into the unsymmetrical alkene category, hence; Markovnikov's rule is applied to this molecule.

Refer to the below reaction;

  CH2=CH(CH2)4CH3H2SO4/H2OCH3CHOH(CH2)4CH3

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation:

The resulting polymer should be identified after polymerization of C7H14.

Concept Introduction:

Alkenes are hydrocarbon molecules that consist a carbon-carbon double bond inside a molecule.

Polymers are high molecular weight macromolecules which formed from covalently bonded monomer molecules.

Answer to Problem 95P

  General, Organic, and Biological Chemistry - 4th edition, Chapter 13, Problem 95P , additional homework tip  4

Explanation of Solution

Polymers are high molecular weight macromolecules which formed from covalently bonded monomer molecules. When forming polymers from alkene monomers, the weak bond which is in the carbon-carbon double bond is broken and new strong bond will form to connect the monomer molecules together. Hence; weak bond of the carbon-carbon double bond of CH2=CH(CH2)4CH3 will break and new strong bond will form to create polyheptane. 'n' number of monomers will together make polyheptane polymer with 'n' number of heptene monomers. Refer to the below diagram;

  General, Organic, and Biological Chemistry - 4th edition, Chapter 13, Problem 95P , additional homework tip  5

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Chapter 13 Solutions

General, Organic, and Biological Chemistry - 4th edition

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