Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 5, Problem 25P

(a)

Interpretation Introduction

Interpretation:

Skeletal structure of the given compound (Z)-1,3,5-tribromo-2-pentene has to be drawn.

Concept introduction:

  • Molecular structure is the arrangement of chemical bonds between atoms in a molecule (or in an ion or radical with multiple atoms), specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.  From the IUPAC name of compound its structure can be easily drawn.
  • IUPAC name consists of three parts in major namely Prefix suffix and root word.
  • Prefix represents the substituent present in the molecule and its position in the root name.
  • Suffix denotes the presence of functional group if any in the molecule.  It can be an alkene, alkyne, alcohol, carboxylic acid, alcohol etc.
  • For alkenes, suffix will be ‘ene’.
  • Root word represents the longest continuous carbon skeleton of the organic molecule.
  • When a molecule consists of cyclic structure, the root word of the molecule is prefixed with cyclo, if it is two cyclic structure combined then prefixed with bicyclo.
    • E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.
    • In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight. If the higher priority groups are on the same sides, then the configuration is designated as Z. If the higher priority groups are on the opposite sides, then the configuration is designated as E. 
    • Skeletal formula: It’s indicated as the line-angle formula or shorted formula of an organic compound is a type of molecular structural formula the indicated of molecular bonding and information its molecular geometry.

(b)

Interpretation Introduction

Interpretation:

Skeletal structure of the given compound (Z)-3-methyl-2-heptene has to be drawn.

Concept introduction:

  • Molecular structure is the arrangement of chemical bonds between atoms in a molecule (or in an ion or radical with multiple atoms), specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.  From the IUPAC name of compound its structure can be easily drawn.
  • IUPAC name consists of three parts in major namely Prefix suffix and root word.
  • Prefix represents the substituent present in the molecule and its position in the root name.
  • Suffix denotes the presence of functional group if any in the molecule.  It can be an alkene, alkyne, alcohol, carboxylic acid, alcohol etc.
  • For alkenes, suffix will be ‘ene’.
  • Root word represents the longest continuous carbon skeleton of the organic molecule.
  • When a molecule consists of cyclic structure, the root word of the molecule is prefixed with cyclo, if it is two cyclic structure combined then prefixed with bicyclo.
    • E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.
    • In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight.  If the higher priority groups are on the same sides, then the configuration is designated as Z.  If the higher priority groups are on the opposite sides, then the configuration is designated as E. 
    • Skeletal formula: It’s indicated as the line-angle formula or shorted formula of an organic compound is a type of molecular structural formula the indicated of molecular bonding and information its molecular geometry.

(c)

Interpretation Introduction

Interpretation:

Skeletal structure of the given compound (E)-1,2-dibromo-3-isopropyl-2-hexene has to be drawn.

Concept introduction:

  • Molecular structure is the arrangement of chemical bonds between atoms in a molecule (or in an ion or radical with multiple atoms), specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.  From the IUPAC name of compound its structure can be easily drawn.
  • IUPAC name consists of three parts in major namely Prefix suffix and root word.
  • Prefix represents the substituent present in the molecule and its position in the root name.
  • Suffix denotes the presence of functional group if any in the molecule.  It can be an alkene, alkyne, alcohol, carboxylic acid, alcohol etc...
  • For alkenes, suffix will be ‘ene’.
  • Root word represents the longest continuous carbon skeleton of the organic molecule.
  • When a molecule consists of cyclic structure, the root word of the molecule is prefixed with cyclo, if it is two cyclic structure combined then prefixed with bicyclo.
    • E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.
    • In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight.  If the higher priority groups are on the same sides, then the configuration is designated as Z.  If the higher priority groups are on the opposite sides, then the configuration is designated as E.
    • Skeletal formula: It’s indicated as the line-angle formula or shorted formula of an organic compound is a type of molecular structural formula the indicated of molecular bonding and information its molecular geometry.

(d)

Interpretation Introduction

Interpretation:

Structure of the given compound Vinyl bromide has to be drawn.

Concept introduction:

  • Molecular structure is the arrangement of chemical bonds between atoms in a molecule (or in an ion or radical with multiple atoms), specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.  From the IUPAC name of compound its structure can be easily drawn.
  • IUPAC name consists of three parts in major namely Prefix suffix and root word.
  • Prefix represents the substituent present in the molecule and its position in the root name.
  • Suffix denotes the presence of functional group if any in the molecule.  It can be an alkene, alkyne, alcohol, carboxylic acid, alcohol etc.
  • For alkenes, suffix will be ‘ene’.
  • Root word represents the longest continuous carbon skeleton of the organic molecule.
  • When a molecule consists of cyclic structure, the root word of the molecule is prefixed with cyclo, if it is two cyclic structure combined then prefixed with bicyclo.
    • E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.
    • In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight.  If the higher priority groups are on the same sides, then the configuration is designated as Z.  If the higher priority groups are on the opposite sides, then the configuration is designated as E. 
    • Skeletal formula: It’s indicated as the line-angle formula or shorted formula of an organic compound is a type of molecular structural formula the indicated of molecular bonding and information its molecular geometry.
    • Vinylic compound contains CH2=CH part.

(e)

Interpretation Introduction

Interpretation:

Skeletal structure of the given compound 1,2-dimethylcyclopentene has to be drawn.

Concept introduction:

  • Molecular structure is the arrangement of chemical bonds between atoms in a molecule (or in an ion or radical with multiple atoms), specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.  From the IUPAC name of compound its structure can be easily drawn.
  • IUPAC name consists of three parts in major namely Prefix suffix and root word.
  • Prefix represents the substituent present in the molecule and its position in the root name.
  • Suffix denotes the presence of functional group if any in the molecule.  It can be an alkene, alkyne, alcohol, carboxylic acid, alcohol etc.
  • For alkenes, suffix will be ‘ene’.
  • Root word represents the longest continuous carbon skeleton of the organic molecule.
  • When a molecule consists of cyclic structure, the root word of the molecule is prefixed with cyclo, if it is two cyclic structure combined then prefixed with bicyclo.
    • E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.
    • In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight.  If the higher priority groups are on the same sides, then the configuration is designated as Z.  If the higher priority groups are on the opposite sides, then the configuration is designated as E. 
    • Skeletal formula: It’s indicated as the line-angle formula or shorted formula of an organic compound is a type of molecular structural formula the indicated of molecular bonding and information its molecular geometry.

(f)

Interpretation Introduction

Interpretation:

Skeletal structure of the given compound diallylamine has to be drawn.

Concept introduction:

  • Molecular structure is the arrangement of chemical bonds between atoms in a molecule (or in an ion or radical with multiple atoms), specifically which atoms are chemically bonded to what other atoms with what kind of chemical bond.  From the IUPAC name of compound its structure can be easily drawn.
  • IUPAC name consists of three parts in major namely Prefix suffix and root word.
  • Prefix represents the substituent present in the molecule and its position in the root name.
  • Suffix denotes the presence of functional group if any in the molecule. It can be an alkene, alkyne, alcohol, carboxylic acid, alcohol etc.
  • For alkenes, suffix will be ‘ene’.
  • Root word represents the longest continuous carbon skeleton of the organic molecule.
  • When a molecule consists of cyclic structure, the root word of the molecule is prefixed with cyclo, if it is two cyclic structure combined then prefixed with bicyclo.
    • E-Z designators are used as like cis-trans terminology for non-similar groups attached alkenes.
    • In E-Z designations, the groups attached to vinylic positions are checked by their priority on the basis of higher molecular weight.  If the higher priority groups are on the same sides, then the configuration is designated as Z.  If the higher priority groups are on the opposite sides, then the configuration is designated as E. 
    • Skeletal formula: It’s indicated as the line-angle formula or shorted formula of an organic compound is a type of molecular structural formula the indicated of molecular bonding and information its molecular geometry.
    • Hydrogen bonded to a vinylic carbon is called vinylic hydrogen, and hydrogen bonded to an allylic carbon is called allylic hydrogen.

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Students have asked these similar questions
Draw the structure of the following compounds.  a. 1-ethyl-3-methylcycloheptane   b. Cyclopropylcyclopentane c. 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane
Show how to convert 1- Butene into these compounds. a. Butane  b. 2- Butanol c. 2- Bromobutane  d. 1,2- Dibromobutane
Draw the structures of the following compounds.

Chapter 5 Solutions

Essential Organic Chemistry, Global Edition

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