SL Reaction pathways Deduce reaction pathway given the starting materials and the product, e.g: CH 3...

SL Reaction pathways

• Deduce reaction pathway given the starting materials and the product, e.g:

CH3CH2OH CH3CH2CHO• Conversions with more than two stages will not

be assessed. Reagents, conditions and equations should be included

• The compound and reaction types in this topic are summarized in the schemes on the next slides

K2Cr2O7

propane

1-chloro-propane

1-propanol

propanal

propanoic acid

propene

polypropene

(M) substitution via radical reaction

(M) substitutionaddition

oxidation

oxidation

+OH-

+HCl

1,2-dichloro-propane

addition+H2


(M) polyaddition

(M) further radical substitution to tri- and tetra-chloropropane

+H2Oaddition

propane

1-chloro-propane

1-propanol

propanal

propanoic acid

propene

polypropene

(M) substitution via radical mechanism. Induced by homolytic cleavage of Cl2 by UV-light



(M) substitution via radical mechanism. Induced by homolytic cleavage of Cl2 by UV-light

Addition reaction.Hydrogen halide (HCl), spontaneous at STP

Addition reaction. H2 and Ni-catalyst

Poly-addition. Radical mechanism. Initiation, prolongation and termination

(M) substitution reaction with NaOH; SN1 or SN2

Oxidation of primary alcohol with acidified K2Cr2O7. Distillation to get the product

Oxidation of primary alcohol with acidified K2Cr2O7. Reflux to get the product


(M) substitution

addition

oxidation

oxidation

+OH-

+HCladdition

+Cl2


(M) polyaddition


C

H

C

H

H

H

C

H

H

OH

H

C

H

C

H

H

H

C

H

H

H

Cl

C

H

C

H

H

H

C

H

H

H

H

C

H

C

H

H

H

C

O

OH

H

C

H

C

H

H

H

C

O

H

H

C

H

C

H

H

H

C

H

H

C

H

C

H

H

H

C

H

H

Cl

Cl

CC

CH3

H H

Hn

carboxylic acid

aldehyde

chloroalkane

alkane

dichloroalkane

alkene

polyalkene

primary alcohol

butane

1-chloro-butane



oxidation

oxidation

+OH-+HCl

addition+H2


(M) polyaddition


What is formed?

propane

2-chloro-propane

2-propanol

propanone

1-propene

polypropene


(M) substitution

addition

oxidation

+OH-+HCl


addition+H2


(M) polyaddition

(M) further radical substitution to tri- and tetra- chloropropane

propane

2-chloro-propane

2-propanol

propanone

1-propene

polypropene


(M) substitution

addition

+OH-

+HCl


addition

+Cl2(M) substitution via radical reaction

(M) polyaddition

(M) further radical substitution to tri- and tetra chloropropane

Oxidation of secondary alcohol with acidified K2Cr2O7



oxidation

+OH-

+HCl

addition

+H2


(M) polyaddition

(M) further radical substitution to tri- and tetra chloropropane

CC

CH3

H H

Hn

C

H

C

H

H

H

C

H

H

C

H

C

H

H

H

C

H

H

Cl

Cl

CC

H

H

H

C

H

H

H

O

C

H

C

H

H

H

C

H

H

H

OH

C

H

C

H

H

H

C

H

H

H

H

C

H

C

H

H

H

C

H

H

Cl

H

ketone

secondary alcohol

secondary chloroalkane

alkanedichloroalkane

alkene

polyalkene

butane

2-chloro-butane

substitution via radical reaction

substitution +OH-

What is formed?

oxidation

Draw structural formula of reactants and products, name them and give reaction pathway

CH3CH2CHOK2Cr2O7

CH3CH=CHCH3

H2

CH3BrNaOH

CH3CH3

UV-light, Cl2

K2Cr2O7

CH3CH=CHCH2CH3

HI

Answers

CH3CH2CHOK2Cr2O7

CH3CH=CHCH3

H2

CH3BrNaOH

CH3CH3

UV-light, Cl2

K2Cr2O7

CH3CH=CHCH2CH3

HI

CH3CH2COOH oxidation

CH3CH2CH2CH3 addition

CH3OH CH2O

CH2ClCH3

substitution oxidation

radical substitution

additionCH3CHICH2CH2CH3

propanal propanoic acid

2-butene butane

methylbromide methanol methanal

ethane chloroethane

2-pentene 2-iodopentane

1-3. Substitution via radical mechanism. Induced by homolytic cleavage of Cl2 by UV-light.

4. Addition reaction. Hydrogen halide, spontaneous at STP 5. Addition reaction. H2 and Ni-catalyst

6. Addition reaction. Halogene, spontaneous at STP 7. Poly-addition. Radical mechanism. Initiation, prolongation and termination 8. Substitution reaction with NaOH; SN1 or SN2

9. Oxidation of primary alcohol with acidified K2Cr2O7. Distillation to get the product

10. Oxidation of primary alcohol with acidified K2Cr2O7. Reflux to get the product

11. Oxidation of secondary alcohol with acidified K2Cr2O7

HL Reaction pathways

1-chloro-propane

1-propanol

propanoic acid

propene

Condensation reaction. Acid catalyst (or alkaline catalyst). Equilibrium reaction.

Condensation reaction. Acid catalyst (or alkaline catalyst, but more common when hydrolysis of ester).Equilibrium reaction.

(M) Substitution reaction. SN1 or SN2 CN-

(M) Elimination reaction. Hot, concentrated and reflux

butanenitrile

1-propyl propanoate

propylamine, butylamine

propyl amide

(M) Substitution reaction. SN1 or SN2 NH3

Reduction with H2 and Ni-catalyst


Condensation

Condensation

(M) Substitution CN-

(M) Elimination

(M) Substitution

Reduction

C

H

C

H

H

H

C

H

H

C

H

C

H

H

H

C

H

H

H

Cl C

H

C

H

H

H

C

H

H

H

NC

C

H

H C

H

H

H

NH2C

H

H

C

H

C

H

H

H

C

H

H

H

NH2C

H

H

C

H

C

H

H

H

C

H

H

OH

H

C

H

C

H

H

H

OH

C OH

C

H

C

H

H

H

OH

C O C

H

C

H

H

HH

C H

H

C

H

C

H

H

H

OH

C N C

H

C

H

H

HH

C H

HH

nitrile

chloropropane

alkene

alcohol

carboxylic acid

amine

amideester

1-chloro-butane

1-butanol

butanoic acid

Condensation reaction. Acid catalyst (or alkaline catalyst). Equilibrium reaction.

Condensation reaction. Acid catalyst (or alkaline catalyst, but more common when hydrolysis of ester).Equilibrium reaction.

substitution CN-

elimination

substitution NH3

reduction H2

What is formed?


1. Elimination reaction. Hot, concentrated and reflux2. Substitution reaction. SN1 or SN2

3. Substitution reaction. SN1 or SN2. (Can be substituted up 4 times to a quarternary ammonum salt)

4. Condensation reaction. Acid catalyst (or alkaline catalyst, but more common when hydrolysis of ester). Equilibrium reaction.

5. Condensation reaction. Acid catalyst (or alkaline catalyst). Equilibrium reaction.

6. Nitrile to amin: Reduction with H2 and Ni-catalyst

6alkene

SL Reaction pathways Deduce reaction pathway given the starting materials and the product, e.g: CH 3...

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