Mechanism of Reaction in Organic Chemistry AS Level Cambridge Examination

Free Radical substitution to all alkanes and alkyl part of organic compound
1. Reagent conditions are:…………or………….. & …………………..

Example 1
Overall equation: C4H10 + Cl2 - C4H8Cl + HCl

2. Reaction Occurs in 3 stages:

a) Initiation reaction
Equation: 
………………………. Fission of ………… bond (endothermic process)
b) Propagation reactions
Equation:


c) Termination reactions

Equation:
Forms reactant: 

Forms product: 

Forms unusual product with double the number of carbons than the reacting alkane :

Exercise 1:Cyclopentane reacts with bromine in the presence of uv light to produce

bromocyclopropane.
Exercise 2: 1-bromoethane reacts with chlorine in the presence of uv light to product
1-bromo-2-chloroethane

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II. Electrophilic Addition of alkene with electrophile
1. Alkene are more reactive than alkane because
a)
b)

2. Electrophiles are ……………. pair acceptors

3. When Br2 bromine reacts with alkene such as propene, CH3CH=CH2,
a) The pi electrons in C=C polarises the Br2 to form partial charges in Br2 molecules
b) Electrophile gains two electrons from C=C to form carbocation and bromide anion
c) Bromide anion attacks carbocation to form a C-Br covalent bond.
d) Mechanism of reaction between propene and bromine in the dark:

 

Exercise 1: 1-butene reacts with HBr to produce Two products, X and Y.

X has higher yield. X shows stereoisomerism
Y has lower yield.
Exercise 2: 3-methylbut-1-ene reacts with steam under special conditions to produce two
products.
Major product is 3-methylbutan-2-ol which shows stereoisomerism.
while minor product is 3-methylbutan-1-ol does not show stereoisomerism.

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III. Nucleophilic substitution.
1. Nucleophiles are ……………… pair donor.
2. Examples of nucleophiles are :
3. Rate of reaction depends on
a) Bond energy ……., size of ……….. atom, shared electron distance from nucleus of
X
4. Reaction between 1-bromobutane and NaOH aqueous and heated. Then
a) 1-bromobutane is a …………………. Halogenoalkane.
b) This is a SN …. Reaction.
c) The nucleophile is ………..
d) Mechanism of reaction via intermediate

 

e) When 1-iodobutane and 1-bromobutane is reacted with NaOH aq mixed with 1cm3
AgNO3 silver nitrate (aq), heated under the same condition
(i) Difference in colour of precipitate:

(ii) Rate of ppt forming:

(iii) Reason : C-I bond energy…………………….., Size Iodine atom is ……… in

C-I
5. Reaction between 2-bromomethylpropane with KCN in ethanol
a) Nucleophile is……………
b) This is a SN…. Reaction because 2-bromomethylpropane is a …………
halogenoalkane.
c) Mechanism of reaction via carbocation because
(i) Alkyl group has ………………………… effect
(ii) …………….alkyl group greater ………………………. Effect
(iii) …………………carbocation is more ………………..
(iv) Positive charge density on C + is ……………………………
d) Mechanism of reaction in two steps

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IV Nucleophilic addition of carbonyl compound with HCN in drops of NaCN/H2SO4/NaOH
1. Nucleophile is ………………..
2. NaCN role stated as ………………………..
3. NaCN role explained……………………………………………………………….
……………………………………………………………………………………..
4. NaOH drops added with reason …………………………………………………..
5. When ethanal reacts with HCN with drops of NaCN
a) The nucleophile is …………………
b) Mechanism of reaction

6. When butanone reacts with HCN drops NaCN , the product exist as a pair of isomers.
a) Mechanism of reaction:

 

b) Reason why a pair of isomers are formed:

(i) A pair of …………………………..isomers are formed.
(ii) The product has a …………… carbon.
(iii) The CN- nucleophile can attack …………….. and …………….. the ……..
C=O in ……………… chance.

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