Rules For Organic Chemical Conversions p3g2n

Chemistry Important rules for Conversions 1

Primary Alcohol

Oxidation

City College

Aldehyde O

K₂Cr₂O₇ H₂SO₄

CH₃ - CH₂ - OH + [O] Ethanol 2

Secondary Alcohol

CH₃ - C – H + H₂O Ethanal

Oxidation

Ketone O

K₂Cr₂O₇ H₂SO₄

CH₃ - CH – CH₃ + [O]

CH₃ - C – CH₃ + H₂O

OH 2-Propanol 3

Propanone

Aldehydes Reduction Primary Alcohol O

H- C – H + H₂ Pd,Pt or Ni CH₃ - OH Formaldehyde Methanol Reduction 4

Ketones

Secondary Alcohol

O CH₃ - C – CH₃ + H₂ Pd,Pt or Ni CH₃ - CH – CH₃ Propanone 5

OH

Formaldehyde + G.R

2-Propanol

Primary Alcohol H

CH₃-CH₂ᵟ⁻ -Mgᵟ⁺-Brᵟ⁻

Cᵟ⁺

+ H

Ether

CH₃-CH₂

Br

H

H H

Oᵟ⁻

Cᵟ⁺

O⁻Mg⁺Br

H₃O⁺

H

CH₃-CH₂

C

OH + Mg

1-Propanol

OH

6

Higher Aldehydes + G.R

Secondary Alcohol H

CH₃-CH₂ᵟ⁻ -Mgᵟ⁺-Brᵟ⁻

Cᵟ⁺

+ CH₃

Ether

Br

H

H CH₃

Cᵟ⁺

O⁻Mg⁺Br

H₃O⁺

CH₃

OH + Mg

C

CH₃-CH₂

CH₃-CH₂

7

Oᵟ⁻

Ketones + G.R

OH

Tertiary Alcohol CH₃

CH₃-CH₂ᵟ⁻ -Mgᵟ⁺-Brᵟ⁻ Ether

CH₃ CH₃

Cᵟ⁺

O⁻Mg⁺Br

Oᵟ⁻

CH₃ CH₃ H₃O⁺

CH₃

Br OH + Mg

C

CH₃-CH₂

CH₃-CH₂

8

Cᵟ⁺

+

CO₂ + G.R

OH

Carboxylic acid

CH₃-CH₂ᵟ⁻ -Mgᵟ⁺-Brᵟ⁻

+ Oᵟ⁻

Cᵟ⁺

O

Ether

O

C

O⁻Mg⁺Br

Br H₃O⁺

O

C

CH₂

CH₂

CH₃

CH₃

OH + Mg OH

9

Epoxide + G.R

Primary Alcohol

CH₃-CH₂ᵟ⁻ -Mgᵟ⁺-Brᵟ⁻

CH₂ᵟ⁺

+

CH₂ᵟ⁺

O

Ether

CH₃-CH₂- CH₂- CH₂- O⁻Mg⁺Br Br

H₃O⁺

CH₃-CH₂- CH₂- CH₂- OH + Mg OH 10 Alcohol + G.R

Alkane

CH₃-CH₂ᵟ⁻ - Mgᵟ⁺-Brᵟ⁻

+

Ether

CH₃-CH₂ᵟ⁺- Oᵟ⁻-Hᵟ⁺ Br

CH₃-CH₃ + Mg OCH₂CH₃ 11 H₂O/NH₃ + G.R

Alkane

CH₃-CH₂ᵟ⁻ - Mgᵟ⁺-Brᵟ⁻

+ Hᵟ⁺ - Oᵟ⁻- H

Ether

Br

CH₃-CH₃ + Mg

OH 12 Alkyl Halide + KOH(aqueous) CH₃ - CH₂ - Cl + KOH(aq.)

Alcohol + KX CH₃ - CH₂ -OH + KCl

13 Alkyl Halide + KOH(alc.) CH₃ - CH₂ - Cl + KOH(alc.)

Alkene+H₂O+KX CH₂ = CH₂ +H₂O + KCl

14 To increase No. of C atoms; a- Wurtz synthesis CH₃-CH₂-Cl+2Na+Cl-CH₂-CH₃ Ether CH₃-CH₂-CH₂-CH₂+2NaCl b- Grignard Reagent Reactions of the rules#5,6,7,8,9 as mentioned on previous pages. 15 To decrease No. of C atoms; a- Decarboxylation with soda lime; O CH₃ - CH₂ - C - O⁻Na⁺ + NaOH b- Ozonolysis; CH₂ = CH₂ + O₃

H₃C - CH₃ + Na₂CO₃ O 2 H- C – H

Important Points; •

Addition reactions of alkenes and alkynes are called Electrophilic addition reactions.

•

Substitution reactions of Benzene are called electrophilic Substitution reactions.

•

Addition reactions of aldehydes and ketones are called Nucleophilic addition reactions. Substitution reactions of alkyl halides are called nucleophilic substitution reactions.

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