Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and...

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Organic Chemistry HL Edition: Reactions of Amines & Nitriles Tuesday, February 21, 2012

Transcript of Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and...

Page 1: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Organic ChemistryHL Edition:

Reactions of Amines & Nitriles

Tuesday, February 21, 2012

Page 2: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

A new functional group!Nitriles are hydrocarbons which contain the C≡N group

Signified by R-CNUse suffix “nitrile” Soluble in water

Tuesday, February 21, 2012

Page 3: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Synthesis of NitrilesNitriles are made by nucleophilic substitution of haloalkanes

Tuesday, February 21, 2012

Page 4: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Reactions Nitriles are important synthetic compounds They can be used to produce ammonia and carboxylic acids

Tuesday, February 21, 2012

Page 5: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Reduction

A reduction reaction involves increasing bonds to hydrogen Note that when you react with a nitriles, you increase the number carbons by one

Tuesday, February 21, 2012

Page 6: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Synthesis of AminesAmines are created by reacting haloalkane with ammonia:

R-X + NH3 → R-NH2 + HX

Tuesday, February 21, 2012

Page 7: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Problem! This reaction doesn’t stop with the primary amine...it keeps goingFor this reason, it is not the favoured method for making amines

Tuesday, February 21, 2012

Page 8: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

SN2 Mechanism of Amine Formation

Tuesday, February 21, 2012

Page 9: Organic Chemistry...halogenoalkane with polar bond transition state with partially formed C—C and C—X bonds nitrile hydrolysis catalysed by acid carboxylic acid + NH3 ammonia bromoalkane

Try it!

Tuesday, February 21, 2012


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