Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 5, Problem 24P

(a)

Interpretation Introduction

Interpretation:

Condensed 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. 
    • Condensed Formula: Molecular formula where the symbols of atoms are listed in order as they appear in the respective molecular structure with bonded dash omitted or limited it is called the condensed structure.

(b)

Interpretation Introduction

Interpretation:

Condensed structure of 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. 
    • Condensed Formula: Molecular formula where the symbols of atoms are listed in order as they appear in the respective molecular structure with bonded dash omitted or limited it is called the condensed structure.

(c)

Interpretation Introduction

Interpretation:

Condensed 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.
    • Condensed Formula: Molecular formula where the symbols of atoms are listed in order as they appear in the respective molecular structure with bonded dash omitted or limited it is called the condensed structure.

(d)

Interpretation Introduction

Interpretation:

Structure of 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. 
    • Condensed Formula: Molecular formula where the symbols of atoms are listed in order as they appear in the respective molecular structure with bonded dash omitted or limited it is called the condensed structure.
    • Vinylic compound contains CH2=CH part.

(e)

Interpretation Introduction

Interpretation:

Condensed 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.
    • Condensed Formula: Molecular formula where the symbols of atoms are listed in order as they appear in the respective molecular structure with bonded dash omitted or limited it is called the condensed structure.

(f)

Interpretation Introduction

Interpretation:

Condensed structure of the given compound diallylamine should 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.
    • Condensed Formula: Molecular formula where the symbols of atoms are listed in order as they appear in the respective molecular structure with bonded dash omitted or limited it is called the condensed structure.
    • 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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Chapter 5 Solutions

Essential Organic Chemistry (3rd Edition)

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