Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 19.15, Problem 42ATS

(a)

Interpretation Introduction

Interpretation:

Reaction of o-bromonitrobenzene with sodium hydroxide at elevated temperature forms only one product. For this reaction –

Structure of the product has to be drawn

Concept Introduction:

  • Aromatic compounds undergo another type of reactions namely Aromatic nucleophilic substitution reactions designated as SNAr .
  • A nucleophile, unlike an electrophile is a species that is electron rich and always attracted towards electron deficient site. A nucleophile is mobile unlike electrophile.
  • The criteria for aromatic nucleophilic substitution reaction to occur are –
  • The aromatic ring must contain a strong electron withdrawing group like nitro group.
  • The aromatic ring must contain a leaving group
  • The leaving group must be posited either ortho or para position to the strong electron withdrawing group.
  • In the mechanism of SNAr reaction the nucleophile attacks the position that is bonded to leaving group and forms a resonance stabilized intermediate called Meisenheimer complex.
  • Let the substituent be ‘X’ that then C-X bond gets broken and  C-Nu bond is formed. The substituent ‘X’ is termed as ‘Leaving group’. A good leaving is large in size with high electron affinity that they are capable to grabbing the bond pair electron and leaving form the aromatic C atom. Halogens are known to be excellent leaving group.
  • The overall reaction can be represented as follows –

                     Organic Chemistry, Chapter 19.15, Problem 42ATS , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

Reaction of o-bromonitrobenzene with sodium hydroxide at elevated temperature forms only one product. For this reaction –

Intermediate formed in the reaction has to be identified.

Concept Introduction:

  • Aromatic compounds undergo another type of reactions namely Aromatic nucleophilic substitution reactions designated as SNAr .
  • A nucleophile, unlike an electrophile is a species that is electron rich and always attracted towards electron deficient site. A nucleophile is mobile unlike electrophile.
  • The criteria for aromatic nucleophilic substitution reaction to occur are –
  • The aromatic ring must contain a strong electron withdrawing group like nitro group.
  • The aromatic ring must contain a leaving group
  • The leaving group must be posited either ortho or para position to the strong electron withdrawing group.
  • In the mechanism of SNAr reaction the nucleophile attacks the position that is bonded to leaving group and forms a resonance stabilized intermediate called Meisenheimer complex.
  • Let the substituent be ‘X’ that then C-X bond gets broken and  C-Nu bond is formed. The substituent ‘X’ is termed as ‘Leaving group’. A good leaving is large in size with high electron affinity that they are capable to grabbing the bond pair electron and leaving form the aromatic C atom. Halogens are known to be excellent leaving group.
  • The overall reaction can be represented as follows –

                     Organic Chemistry, Chapter 19.15, Problem 42ATS , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

Reaction of o-bromonitrobenzene with sodium hydroxide at elevated temperature forms only one product. For this reaction –

Feasibility of the reaction if the reactant is m-bromonitrobenzene.

Concept Introduction:

  • Aromatic compounds undergo another type of reactions namely Aromatic nucleophilic substitution reactions designated as SNAr .
  • A nucleophile, unlike an electrophile is a species that is electron rich and always attracted towards electron deficient site. A nucleophile is mobile unlike electrophile.
  • The criteria for aromatic nucleophilic substitution reaction to occur are –
  • The aromatic ring must contain a strong electron withdrawing group like nitro group.
  • The aromatic ring must contain a leaving group
  • The leaving group must be posited either ortho or para position to the strong electron withdrawing group.
  • In the mechanism of SNAr reaction the nucleophile attacks the position that is bonded to leaving group and forms a resonance stabilized intermediate called Meisenheimer complex.
  • Let the substituent be ‘X’ that then C-X bond gets broken and  C-Nu bond is formed. The substituent ‘X’ is termed as ‘Leaving group’. A good leaving is large in size with high electron affinity that they are capable to grabbing the bond pair electron and leaving form the aromatic C atom. Halogens are known to be excellent leaving group.
  • The overall reaction can be represented as follows –

                     Organic Chemistry, Chapter 19.15, Problem 42ATS , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

Reaction of o-bromonitrobenzene with sodium hydroxide at elevated temperature forms only one product. For this reaction –

Feasibility of the reaction if the reactant is p-bromonitrobenzene.

Concept Introduction:

  • Aromatic compounds undergo another type of reactions namely Aromatic nucleophilic substitution reactions designated as SNAr .
  • A nucleophile, unlike an electrophile is a species that is electron rich and always attracted towards electron deficient site. A nucleophile is mobile unlike electrophile.
  • The criteria for aromatic nucleophilic substitution reaction to occur are –
  • The aromatic ring must contain a strong electron withdrawing group like nitro group.
  • The aromatic ring must contain a leaving group
  • The leaving group must be posited either ortho or para position to the strong electron withdrawing group.
  • In the mechanism of SNAr reaction the nucleophile attacks the position that is bonded to leaving group and forms a resonance stabilized intermediate called Meisenheimer complex.
  • Let the substituent be ‘X’ that then C-X bond gets broken and  C-Nu bond is formed. The substituent ‘X’ is termed as ‘Leaving group’. A good leaving is large in size with high electron affinity that they are capable to grabbing the bond pair electron and leaving form the aromatic C atom. Halogens are known to be excellent leaving group.
  • The overall reaction can be represented as follows –

                     Organic Chemistry, Chapter 19.15, Problem 42ATS , additional homework tip  4

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Chapter 19 Solutions

Organic Chemistry

Ch. 19.7 - Prob. 11CCCh. 19.7 - Prob. 12CCCh. 19.8 - Prob. 13CCCh. 19.9 - Prob. 14CCCh. 19.9 - Prob. 15CCCh. 19.10 - Prob. 1LTSCh. 19.10 - Prob. 16PTSCh. 19.10 - Prob. 17ATSCh. 19.10 - Prob. 18ATSCh. 19.11 - Prob. 2LTSCh. 19.11 - Prob. 19PTSCh. 19.11 - Prob. 20ATSCh. 19.11 - Prob. 21ATSCh. 19.11 - Prob. 3LTSCh. 19.11 - Prob. 22PTSCh. 19.11 - Prob. 23ATSCh. 19.11 - Prob. 24ATSCh. 19.11 - Prob. 4LTSCh. 19.11 - Prob. 25PTSCh. 19.11 - Prob. 26ATSCh. 19.11 - Prob. 27ATSCh. 19.12 - Prob. 28CCCh. 19.12 - Prob. 29CCCh. 19.12 - Prob. 5LTSCh. 19.12 - Prob. 30PTSCh. 19.12 - Prob. 31ATSCh. 19.12 - Prob. 32ATSCh. 19.12 - Prob. 6LTSCh. 19.12 - Prob. 33PTSCh. 19.12 - Prob. 34ATSCh. 19.13 - Prob. 35CCCh. 19.13 - Prob. 36CCCh. 19.13 - Prob. 37CCCh. 19.14 - Prob. 38CCCh. 19.14 - Prob. 39CCCh. 19.15 - Prob. 7LTSCh. 19.15 - Prob. 40PTSCh. 19.15 - Prob. 41PTSCh. 19.15 - Prob. 42ATSCh. 19 - Prob. 43PPCh. 19 - Prob. 44PPCh. 19 - Prob. 45PPCh. 19 - Prob. 46PPCh. 19 - Prob. 47PPCh. 19 - Prob. 48PPCh. 19 - Prob. 49PPCh. 19 - Prob. 50PPCh. 19 - Prob. 51PPCh. 19 - Prob. 52PPCh. 19 - Prob. 53PPCh. 19 - Prob. 54PPCh. 19 - Prob. 55PPCh. 19 - Prob. 56PPCh. 19 - Prob. 57PPCh. 19 - Prob. 58PPCh. 19 - Prob. 59PPCh. 19 - Prob. 60PPCh. 19 - Prob. 61PPCh. 19 - Prob. 62PPCh. 19 - Prob. 63PPCh. 19 - Prob. 64PPCh. 19 - Prob. 65PPCh. 19 - Prob. 66PPCh. 19 - Prob. 67PPCh. 19 - Prob. 68PPCh. 19 - Prob. 69PPCh. 19 - Prob. 70PPCh. 19 - Prob. 71PPCh. 19 - Prob. 72PPCh. 19 - Prob. 73PPCh. 19 - Prob. 74IPCh. 19 - Prob. 75IPCh. 19 - Prob. 76IPCh. 19 - Prob. 77IPCh. 19 - Prob. 78IPCh. 19 - Prob. 79IPCh. 19 - Prob. 80IPCh. 19 - Prob. 81IPCh. 19 - Prob. 82IPCh. 19 - Prob. 83IP
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