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Organic Chemistry Synthesis of benzene

by: Megan steltz

Organic Chemistry Synthesis of benzene Chem 372-0

Marketplace > Eastern Michigan University > Chemistry > Chem 372-0 > Organic Chemistry Synthesis of benzene
Megan steltz
GPA 3.28

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About this Document

these notes cover the synthesis of benzene as well as more reactions benzene can perform including diazonium salt
Organic Chemistry
Gregg M. Wilmes
Class Notes
Organic Chemistry, Benzene, synthesis, diazonium, salt
25 ?




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This 26 page Class Notes was uploaded by Megan steltz on Friday October 14, 2016. The Class Notes belongs to Chem 372-0 at Eastern Michigan University taught by Gregg M. Wilmes in Fall 2016. Since its upload, it has received 3 views. For similar materials see Organic Chemistry in Chemistry at Eastern Michigan University.

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Date Created: 10/14/16
Chapter 18 Synthesis of Benzene Reactions of substituted benzene 1. Y can be activating or deactivating a. rate of reaction b. If Y is electron donating its activating c. If Y is electron withdrawing is deactivating 2) Directing effect ● some Y groups are ortho/ para directing ● some Y groups are meta directing ● Activating = ortho/ para ● Deactivating = meta ( unless a halogen then ortho / para) Resonance donating ● Resonance donating places – charge in ortho and para positions ● For O and N resonance donating is stronger then inductive withdrawing ● For F, Cl, Br, I inductive effects are stronger than resonance donating effects Resonance withdrawing groups ● Most common C=O or N=O 1) activating ortho / para directors ● they are inductively withdrawing weak and resonance donating strong ● most activating to least activating ● NH2 , NHR, NK2 > OH > OR > NHCOR > R 2) Deactivating ortho/ para ● -F, -Cl, -Br, -I ● Inductively withdrawing strong ● Resonance donating weak 3) Deactivating meta directors ● Inductively and resonance withdrawing strong ● Least activating to most activating ● -CHO < COR (ketones) < COOR (esters) < COOH (carboxylic acids) < N triple bonded C (nitriles) < SO3H (sulfonyl) < NO2 (nitro) < NR3+ (quaternary ammonium) ● Partial + on ortho / para positions ● Meta positions are less + and more reactive ● No deactivating ortho/ para directors as shown in the resonance structure above. ● Inductive withdrawing is stronger than resonance donating Stronger activating groups ( NH2, OH) result in multiple halogenations For mono- halogenation leave out the catalyst Friedel-Crafts acylation/ alkylation ● Does not reacted with meta deactivator Lewis acid catalyst (AlCl3) reacts with base substituents ● Alkylations lead to poly-alkylated products ● Use large excess of starting material to mono-alkylate If multiple groups are in conflict the most activating or least deactivating controls direction. Reactions on benzene substituents 1) benzylic bromination ● Radical reactions occur with NBS and hv or Δ ● Replaces single benzylic H with Br 2) Oxidation of benzylic hydrogen ● Compounds with benzylic H’s can be oxidized into carboxylic acid with KMnO4 3)Reduction of aryl ketones 4) Reduction of NO2 to NH2 ● Three different reagents can be used H2, Pd-C or Fe, HCl or Sn, HCl Synthesis problem Nitrous acid (HONO) ● Formed by the reaction of HCl + NO2- o Nitrite NaNO2 H-O-N=O + HCl Nitrous acid H2O + N=O Nitrosonium ion 7 different reactions can occur with diazonium salt Synthesis Problem Chapter 18 Synthesize of Benzene Reactions of substituted benzene  1. Y can be activating or deactivating  a. rate of reaction b. If Y is electron donating its activating c. If Y is electron withdrawing is deactivating  2) Directing effect   some Y groups are ortho/ para directing   some Y groups are meta directing  Activating = ortho/ para  Deactivating = meta ( unless a halogen then ortho / para)  Resonance donating   Resonance donating places – charge in ortho and para positions  For O and N resonance donating is stronger then inductive withdrawing   For F, Cl, Br, I inductive effects are stronger than resonance donating effects    Resonance withdrawing groups   Most common C=O or N=O 1) activating ortho / para directors   they are inductively withdrawing weak and resonance donating strong  most activating to least activating  NH2 , NHR, NK2 > OH > OR > NHCOR > R            2) Deactivating ortho/ para  ­F, ­Cl, ­Br, ­I  Inductively withdrawing strong  Resonance donating weak 3) Deactivating meta directors   Inductively and resonance withdrawing strong  Least activating to most activating  ­CHO < COR (ketones) < COOR (esters) < COOH (carboxylic acids)  < N triple bonded C (nitriles) < SO3H (sulfongl) < NO2 (nitro) <  NR3+ (quaternary ammonium)   Partial + on ortho / para positions   Meta positions are less + and more reactive   No deactivating ortho/ para directors as shown in the resonance structure  above.  Inductive withdrawing is stronger than resonance donating  Stronger activating groups ( NH2, OH) result in multiple halogenations For mono­ halogenation leave out the catalyst  Friedel­Crafts acylation/ alkylation   Does not reacted with meta deactivator  Lewis acid catalyst (AlCl3) reacts with base substituents    Alkylations lead to poly­alkylated products  Use large excess of starting material to mono­alkylate  If multiple groups are in conflict the most activating or least deactivating controls  direction. Reactions on benzene substituents  1) benzylic bromation   Radical reactions occur with NBS and hv or Δ  Replaces single benzylic H with Br 2) Oxidation of benzylic hydrogen   Compounds with benzylic H’s can be oxidized into carboxylic acid with  KMnO4 3)Reduction of aryl ketones  4) Reduction of NO2 to NH2  Three different regents can be used H2, Pd­C or Fe, HCl or Sn, HCl Synthesis problem  Nitrous acid (HONO)  Formed by the reaction of HCl + NO2­  o Nitrite NaNO2 H­O­N=O + HCl Nitrous acid H2O + N=O Nitrosonium ion  7 different reactions can occur with diazonium salt Synthesis Problem 


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