Handout: Organic Chemistry Reactions

[Pages:4]Handout: Organic Chemistry Reactions

Reactions Organized by Compound Families

Alkanes 1. Combustion 2. Halogenation Alkenes and Alkynes 1. Additions: hydrogenation, halogenation,

hydrohalogenation, hydration 2. Polymerization Aromatic Compounds Substitutions: nitration, halogenation, sulfonation Alcohols 1. Elimination: dehydration 2. Oxidations Thiols Oxidation Amines Acid-Base reactions Aldehydes and Ketones 1. Addition: Acetal/hemiacetal formation by alcohol

addition (Reverse rxn: Acetal hydrolysis with acid) 2. Oxidation and Reduction for aldehydes (*Ketones go through reduction only) Carboxylic Acids 1. Substitutions: esterification, amidation (Reverse rxns: ester hydrolysis with acid or base, amide hydrolysis with acid or base) 2. Acid-base reactions Phosphoric acid and Phosphates Phosphoric acid: Esterification with alcohol Phosphates: Phosphorylation

H. Kim for Chem 30B 1

Family

Reactions Organized by Reaction Type

Reaction

Example

1. ADDITION Alkenes and Hydrogenation alkynes

Halogenation

Hydrohalogenation

Hydration

Aldehydes and ketones

Addition of alcohol to get hemiacetals or acetals

H

H

Pd catalyst

C C + H2

H

H

H C C H + 2 H2 Pd catalyst

HH HCCH

HH HH HCCH

HH

H

H

CC

H

H

+ Cl2 (or Br2)

Cl Cl HCCH

HH

H

H

CC

+ HCl (or HBr)

H

CH3

H Cl HCCH

H CH3

Markonikov's Rule applies: H adds to C with more Hs already.

H

H

CC

H

CH3

+ H2O

H+ catalyst

H OH HCCH

H CH3

Markonikov's Rule applies.

O H+ catalyst

H3C C H(R) + CH3CH2OH

OH H3C C H(R) + CH3CH2OH

O CH2CH3

hemiacetal

H+ catalyst

O CH2CH3 H3C C H(R)

O CH2CH3 acetal

+ H2O

2. SUBSTITUTION

Aromatic

Nitration

compounds

Halogenation

Sulfonation

Carboxylic acids

Phosphoric acid and Phosphates

Esterification with alcohol

Amidation with amine Phosphoric acid: Esterification with alcohol Phosphates: Phosphorylation

H2SO4 catalyst

+ HNO3

NO2

FeCl3 (or FeBr3) catalyst

Cl

+ Cl2 (or Br2)

H2SO4 catalyst

+ SO3

SO3H

O

H+ catalyst

O

H3C C OH + CH3CH2OH

H3C C OCH2CH3 + H2O

O H3C C OH + CH3NH2

O

heat

O H3C C NHCH3 + H2O O

HO P OH + CH3OH

HO P OCH3 + H2O

OH

OH

OO O

Adenosine O P O P O P O- + ROH

O-

O-

O-

OO

O

Adenosine O P O P O- + RO P O- + Energy

O- O-

O-

H. Kim for Chem 30B 2

3. ELIMINATION

Alcohols

Dehydration

H 3C

H C H

OH

H2SO4 catalyst H

C CH3

C H 3C

H

C CH3 H

+ H3C

H C H

C H

CH2 + H2O

major

minor

Zaitsev's Rule applies: More highly substituted alkene is major

product.

4. OXIDATION/REDUCTION

Alcohols

Oxidation

Thiols Aldehydes

Oxidation Oxidation

Ketones

Reduction (also addition)

Reduction (also addition)

OH

[O]

1? R C H

H

O RCH aldehyde

[O]

O

R C OH

carboxylic acid

OH

2? R C H

R

OH

3? R C H

[O]

O

RCR

Ketone

[O] No Rxn

R

[O] 2 RSH

R-S-S-R

[H]

Reverse rxn: R-S-S-R

O

[O]

RCH

O R C OH

aldehyde

carboxylic acid

O

[H]

RCH

OH RCH

O

[H]

R C CH3

H OH R C CH3 H

2 RSH

5. ACID-BASE

Amines

Rxn with water

(Basic)

Neutralization

with strong acid

to get ammonium

ion or salt

Carboxylic Rxn with water

acids

(Acidic)

Neutralization

with strong base

to get carboxylic

acid salt

Phenols

Neutralization

(very weakly with strong base

acidic)

to get salt

CH3CH2NH2 + H2O

CH3CH2NH

+ 3

+

OH?

CH3CH2NH2 + H3O+ CH3CH2NH2 + HCl

CH3CH2NH3+ + H2O

CH3CH2NH

+ 3

Cl?

Reverse rxn: ammonium ion or salt + base

CH3CH2NH3+ Cl? +

NaOH

CH3CH2NH2 + NaCl + H2O

O H3C C OH

+ H2O

O

H3C C OH (aq) + NaOH (aq)

O H3C C O? + H3O+

O H3C C O? Na+(aq) + H2O

OH + NaOH

O?Na+ + H2O

H. Kim for Chem 30B 3

Other Reaction Types

Family

Reaction

Example

RADICAL REACTIONS

Alkanes

Combustion

(Also

oxidation/reduction

reaction)

Halogenation

Alkenes

Polymerization

heat CH4(g) + 2O2(g)

CO2 + 2H2O + Heat

light or heat

Cl

CH3CH2CH3 + Cl2

HCl + CH3CH2CH2Cl + CH3CHCH3

Cl

Cl

+ CH2CH2CH2 +

Cl Cl

+

CH2CHCH3

Cl CH3CCH3 +

Cl

Cl CHCH2CH3 Cl

Mixed products

CH3CH

initiator CH2

CH3 H2

(C C

H

CH3

C

H2 C

)

H

HYDROLYSIS

Esters (Reverse rxns of

Acid hydrolysis to get carboxylic acid and

O

H+ catalyst

R C O CH3 + H2O

O R C OH + CH3OH

carboxylic acid

alcohol

esterification)

Saponification: Base hydrolysis to get carboxylic acid salt and

O

R C O CH3 + NaOH (aq) H2O

O R C O? Na+ + CH3OH

alcohol

Amides (Reverse rxns of carboxylic acid amidation)

Acid hydrolysis to get amine

Base hydrolysis to get amine

H 3C

O C

H N

CH3

+ H2O

H+ catalyst

O

H3C C

H N CH3 + NaOH (aq)

H2O

O H3C C OH + CH3NH2

O H3C C OH + CH3NH2

Acetals (Reverse reaction of acetal formation

Acid hydrolysis to get aldehydes of ketones (reverse of acetal

H 3C

H C

O

CH2CH3

H+ catalyst + H2O

H 3C

O C

OH + 2 CH3CH2OH

O CH2CH3

from

formation)

aldehydes/ketones)

*Note that organic chemistry reactions can be classified in several different ways.

H. Kim for Chem 30B 4

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