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Cheatography

Haloalkane / Alkyl halides Cheat Sheet (DRAFT) by

Chemical reactions involving haloalkane / Alkyl halides

This is a draft cheat sheet. It is a work in progress and is not finished yet.

Synthesis : Haloge­nation of Alkanes

Reagent
Cl₂ / Br₂
Condition
heat / UV light
Mechanism
free radical substi­tution
Equation
CH₄ + Cl₂ → CH₃Cl + HCl

Synthesis : Hydroh­alo­gen­ation of Alkenes

also known as
Addition of hydrogen halides
Reagent
HCl / HBr / HI
Equation
CH₃CH₂­CH=CH₂ + HCl → CH₃CH₂­CHC­l-CH₃
 
(every product must be shown)

follow Markov­nikov's rule : halogen added to doubly bonded carbon atom attached to the least H atoms

Dehydr­oha­log­enation

Reagent
NaOH / KOH
Condition
ethanol, reflux
Mechanism
Elimin­ation Reaction
Equation
haloalkane + NaOH → alkene
 
(every product must be shown)
follow Zaitsev rule : doubly bonded carbon atom in alkenes bonded to the most number of alkyl groups is major products

Dehydr­oha­log­enation

 

Synthesis : Haloge­nation of Alkenes

Reagent
Cl₂ / Br₂
Condition
CCl₄
Equation
CH₃CH=­CHCH₃ + Cl₂ → CH₃CHC­l-C­HClCH₃

Hydrolysis

Reagent
aqueous NaOH / KOH
Condition
boiling
Mechanism
Nucleo­philic Substi­tution
Equation
haloal­kanes + NaOH → alcohol + NaCl

for carbons bonded to 2 halogens
Equation
CH₃CHCl₂ + NaOH → CH₃CH(OH)₂
 
CH₃CH(OH)₂ → CH₃CH=O (loss of water)

Hydrolysis