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Mechanims-Practice 3

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Hamdy Soliman
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11 views19 pages

Mechanims-Practice 3

Uploaded by

Hamdy Soliman
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Types of reactions and

reaction mechanisms
Aliphatic/alicyclic
1. Free radical substitution (alkanes)
2. Electrophilic addition (alkenes)
3. Nucleophilic substitution (alcohols and haloalkanes)
4. Nucleophilic addition (aldehydes/ketones)
5. Oxidation of alcohols
6. Elimination of alcohols

Aromatic
Electrophilic substitution
Free radical substitution
Alkane + halogen  haloalkane + hydrogen halide

CH4 + Cl2  CH3Cl + HCl

(a) Write the mechanism for the formation of chloromethane.


Reminder: there are 3 stages – initiation, propagation and termination.
(b) Give the condition required for the reaction
(c) State the type of bond fission taking place in the initiation stage.
(b) UV light
(c) Homolytic bond fission

Now do the mechanism for the below equation


CH3CH3 + IBr  CH3CH2Br + HI
Electrophilic addition of alkenes
Ethene + bromine  1,2-dibromoethane

(a) Write a symbol equation for the above reaction


(b) Draw the mechanism for the reaction (include charges, dipoles and curly
arrows).
(c) Give an observation for the reaction
Now do the mechanism for the reaction between propene and HBr to form the major
product.
Nucleophilic substitution
CH3CH2Cl + NaOH  CH3CH2OH + NaCl

(a) State the nucleophile in the above reaction.


(b) Draw the mechanism for the reaction.
OH- is the nucleophile (electron pair donor)

Methanol is reacted with sodium bromide and sulfuric acid. Write an equation/s for
the reactions taking place and apply yourself to draw the mechanism for the
reaction.
Nucleophilic addition of
ketones/aldehydes
HCHO + 2[H]  CH3OH
NaBH4(aq) is required for the conversion of methanal into methanol.

(a) State the nucleophile in the reaction


(b) What is the role of NaBH4
(c) Draw the mechanism for the reaction.
(a) H- (hydride ion)
(b) Reducing agent

Note: dipoles on water


are required
(CH3)2CO + HCN  C(OH)(CH3)CH3CN

(a) State the reagents and conditions required for above reaction
(b) Draw the mechanism for the reaction using CN- as the nucleophile
(c) Name the product made
Note: Do include the
methyl groups

(a) NaCN/H2SO4
(b) 2-hydroxy-2-methyl propane nitrile
Oxidation of alcohols
Butan-1-ol is oxidised using acidified potassium dichromate under
different conditions.

(a) State the role of potassium dichromate


(b) Write an equation for the oxidation of butan-1-ol under distillation conditions.
(c) Write an equation for the oxidation of butan-1-ol under reflux
(d) Give the colour change for the reaction.
(e) Draw an isomer of butan-1-ol that forms a ketone when oxidised using the same
reagents under reflux.
(f) Draw an isomer of butan-1-ol that cannot be oxidised using the above reagents.
(a) Oxidising agent
(b) CH3CH2CH2CH2OH + [O]  CH3CH2CH2CHO + H2O
(c) CH3CH2CH2CH2OH + 2[O]  CH3CH2CH2COOH + H2O
(d) Orange  green (Cr6+ -> Cr3+)
(e) CH3CH2CHOHCH3
(f)
Elimination of alcohols
Butan-1-ol  But-1-ene + water

(a) State the reagents and conditions required to carry out the above reaction.
(b) Write a symbol equation for the reaction.
(c) Butan-2-ol undergoes dehydration. Draw and name all the products that are
made.
(a) Heat under reflux, concentrated sulfuric acid/phosphoric acid.
(b)

+ H2O

(c)

Now draw the dehydration


products of
Electrophilic substitution
• Benzene + chlorine  chlorobenzene + hydrogen chloride

(a) Write a symbol equation for the reaction above.


(b) AlCl3 is required for the reaction. State the role of AlCl3 in the reaction.
(c) Draw the mechanism for the reaction.

(d) A student wanted to make phenylethanone starting from benzene.


State all the reagents and conditions for the reaction.
(e) Write an equation for the formation of the electrophile in question (d).
(a)

(b) Halogen carrier (also catalyst) – reacts with Cl2 to make the electrophile (Cl+
ion)
(c)
Cl+ Cl
Cl
(d) e.g. ethanoyl chloride, AlCl3
(e) CH3COCl + AlCl3  CH3CO+ + AlCl4-

Now do:
Another student wanted to make 4-nitro methylbenzene starting from
methylbenzene. State how the student could go about doing this.
You need to include all the reagents and conditions, all equations (to create the
electrophile, regenerate catalyst, and a full equation for the reaction) and name
and draw the mechanism for the reaction.

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