Summary of Organic Reactions

SUMMARY OF ORGANIC REACTIONS COMPOUND NAME OF REAGENT PROCESS 1. ALKANE Halogenation halogen, X2

uv or sunlight

Haloalkane + HCl

2. ALKENE

RT

Dihalide

C

Halogenation

X2

PRODUCT

CONDITION

C

C

C

X X

Hydrogenation

H2

RT

Alkane C

C

H H

Hydration Apply Markovnikov’s Rule to Unsymmetrical alkene

CHEM II TYPE OF REACTION Free radical substitution

H 2O

H2SO4

Alcohol C

Electrophilic addition

C

OH H

Hydrohalogenation HX

RT

Haloalkane C

C

X H

Mild oxidation

KMnO4/OH-

RT or below

Diol C

C

OHOH

Strong oxidation

KMnO4/H+

Heat

Carbonyl or

Oxidation

C O +O C

carboxylic acid

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COMPOUND 3 (i) BENZENE

3 (ii) METHYLBENZENE

NAME OF PROCESS Nitration

REAGENT

CONDITION

Halogenation

Conc. HNO3 + conc. H2SO4 X2

Alkylation Halogenation

CH3Cl Excess X2

Hydrogenation

Excess H2

T: 500C – 600C AlCl3 or FeCl3 (if X is Cl2) AlCl3 or FeCl3 Uv or sunlight, heat Ni as catalyst High T, high P

Ring reaction: Nitration

Halogenation

Conc. HNO3 + conc. H2SO4

T: 300C

X2

AlCl3 or FeCl3 (if X is Cl2)

PRODUCT

TYPE OF REACTION

C6H5NO2 + H2O Electrophilic substitution

C6H5Cl + HCl C6H5CH3 + HCl C6H6X6

Addition

C6H12

CH3 + O2N

CH3

NO2 CH3 + Cl

CH3

Electrophilic substitution

Cl

Side chain reaction: Halogenation

X2

Uv or sunlight

CH2Cl

Oxidation

KMnO4/H+

Heat

COOH

Free radical substitution

Oxidation

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COMPOUND 4. (i)HALOALKANE C H

NAME OF PROCESS Hydrolysis

C

X

With NH3

With CN-

REAGENT

CONDITION

PRODUCT

H2O or alkaline (aq) (eg. NaOH or KOH)

Heat

Alcohol

NH3

Heat strongly

KCN in ethanol

C

Heat

Amines (mixtures) C

C

H

NH2

C H

C

Heat

RT

C

Elimination

Carboxylic acid H

LiAlH4

CN

Alkene

C

CN

Reduction

C

C

Boil

Nucleophilic substitution

Nitrile H

(ii) NITRILE

C

H OH

C

dehydrohalogenation Alkaline (in ethanol) (eg. NaOH in ethanol or KOH in ethanol) Hydrolysis Dilute sulphuric acid

TYPE OF REACTION

Oxidation

C

COOH

Amines C

C

Reduction

CH2NH2

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FAB/ESM 1324/CHEM 2/ENGINEERING

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COMPOUND 5. (i) ALCOHOL C

NAME OF PROCESS Halogenation

C

H OH

Salt formation

REAGENT HX or NaX + conc. H2SO4 or PCl5 or PCl3 or PBr3 Na

CONDITION RT

PRODUCT Haloalkane C H

RT

C

C

CHI3 (yellow precipitate) and sodium alkanoate salt

RCOOH Or RCOCl

H+, heat

Ester – RCOOR (pleasant smelling)

RT

C

Nucleophilic substitution

acid base reaction

ONa

Warm

H C OH

Esterification

X

I2 and NaOH(aq)

*only +ve for C2H5OH and 20 with structure:

CH3

C

Sodium alkoxide and H2 H

Iodoform reaction

TYPE OF REACTION

C

O C R O + H2O or HCl 20
Ketone 10
Aldehyde

Substitution

H

Oxidation *only 10 and 20 Alcohol can be oxidised

K2Cr2O7/H+

Warm

K2Cr2O7/H+

Heat

KMnO4/H+ Page 4 of 6

FAB/ESM 1324/CHEM 2/ENGINEERING

20
Ketone 10
RCOOH

Oxidation

10
Carboxylic acid 8/6/2009

COMPOUND (ii) PHENOL

OH

Dehydration

Conc. H2SO4

T > 1700C

NAME OF PROCESS Ring reaction Halogenation

REAGENT

CONDITION

Br2(aq)

RT

Alkene

Elimination

PRODUCT

OH

Br

Br

Br

+ 3HBr

white ppt.

Nitration *FeCl3 is another distinguishing test for phenol.

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Dilute HNO3

RT

OH

NO2 +

TYPE OF REACTION

OH

Electrophilic substitution

NO2 Side chain Salt formation Esterification

Na NaOH RCOCl only!! (for your syllabus)

RT RT RT

FAB/ESM 1324/CHEM 2/ENGINEERING

C6H5ONa + H2 C6H5ONa + H2O O O C R

Acid base reaction Substitution

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COMPOUND

6. CARBONYL

O C

NAME OF PROCESS

With HCN

REAGENT

HCN

CONDITION

RT

PRODUCT

Cyanohydrin OH

Oxidation * only aldehydes can be oxidised Reduction

(i) Tollen’s reagent (i) Fehling’s reagent. (iii) K2Cr2O7/H+ (iv) KMnO4/H+ (v) KMnO4/OHLiAlH4 or NaBH4

RT

Condensation

2,4-DNP

RT

O2N

H N NH2 NO2

C

CN

Silver mirror Red brown ppt Orange
green Purple
colourless Purple
brown ppt. Ald
10 alcohol Ketone
20 alcohol -2,4dintrophenylhydrazone H O2N N N C

TYPE OF REACTION

Nucleophilic addition

Oxidation

Reduction

Additionelimination

NO2

7.CARBOXYLIC ACID

C

O OH

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Iodoform I2 and NaOH(aq) *Only ethanal And ketones with –CH3 gp. Salt Na formation NaOH Na2CO3 Esterification R-OH Formation of PCl5 , SOCl2 acyl chloride

warm

RT RT RT H+, heat RT

FAB/ESM 1324/CHEM 2/ENGINEERING

Orange ppt CHI3 (yellow precipitate) and sodium alkanoate salt Salt + H2 Salt + H2O Salt + H2O + CO2 Ester (RCOOR) Acyl chloride O C Cl

Acid base reaction Substitution Substitution

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