Organic reaction maps

Task 1. Highlight all oxidations red, reductions blue, substitutions

green and additions or eliminations yellow
propylamine propanenitrile

propan-1-ol
propanamide
propanal

propan-2-ol propanoic acid

propane

chloropropane ethylpropanoate
propanone

propanoyl chloride
propene

propanoic acid
anhydride
 Task 1. Answers

propylamine propanenitrile

propan-1-ol
propanamide
propanal

propan-2-ol propanoic acid

propane

chloropropane ethyl propanoate

propanone

propanoyl chloride
propene

propanoic acid
anhydride
 Task 2. Draw the correct structures alongside the names

propylamine propanenitrile

propan-1-ol
propanamide
propanal

propan-2-ol propanoic acid

propane

chloropropane ethyl propanoate

propanone

propanoyl chloride
propene

propanoic acid anhydride

 Task 2. Answers
propanenitrile
propylamine
H2 H2
H3C C C NH2
propanamide
O
propan-1-ol
H2
H2 H2 H3C C C NH 2
H3C C C OH propanal
O
H2 propanoic acid
H3C C
propan-2-ol
propane OH H
O
H2
H2 H3C C C
H3C C CH3 H3C CH CH 3
OH

chloropropane ethyl propanoate

H2 H2 O
H3C C C Cl H2
H3C C C
or propanone H2
H O C CH 3
H3C C CH 3 O

Cl propanoyl chloride
H3C CH 3 O
H2
H3C C C
propene
Cl
H
H3C C CH2
propanoic acid anhydride
O O
H2 H2
H3C C C O C C CH3
 Task 3. Label all arrows with reagents and conditions

propylamine propanenitrile

propan-1-ol
propanamide
propanal

propan-2-ol propanoic acid

propane

K2Cr2O7 /
H2SO4 reflux

chloropropane ethyl propanoate

propanone

propanoyl chloride
propene

propanoic acid
anhydride
 Task 4. Draw in arrows for all the reactions you have met and label with
reagents and conditions. Use a red colour to show oxidations and a blue
colour for reductions
propylamine propanenitrile

propan-1-ol
propanamide
propanal

propan-2-ol propanoic acid

propane

K2Cr2O7 /
H2SO4 reflux

chloropropane ethyl propanoate

propanone

propanoyl chloride
propene

propanoic acid
chloride
 Tasks 3 and 4. Answers
H2 Nickel
propylamine catalyst propanenitrile

H2O / HCl
K2Cr2O7 / cold
NH3 H2SO4 distil H2O / HCl
propan-1-ol off product heat
K2Cr2O7 / propanamide
H2SO4
propanal reflux

H2O / NaOH
1. LiAlH4 (ether)
propan-2-ol propanoic acid
propane 2. H2O

Ethanol /
K2Cr2O7 /
H2SO4 reflux
H2SO4 reflux
NH3
SOCl2 H2O
chloropropane ethyl propanoate
H2O / KOH in propanone
Al2O3 heat H2SO4 ethanol ethanol
heat

HCl 1. LiAlH4 (ether)

2. H2O propanoyl chloride
H2 Nickel
propene H2O / H2SO4
catalyst
Ethanol /
H2SO4 reflux

Addition or
elimination substitution propanoic acid
anhydride
oxidation Reduction
 Task 1. Highlight all oxidations red, reductions blue, substitutions
green and additions or eliminations yellow
H2 H2
H3C C C NH2

H2 H2
H3C C C OH
O
O H2
H2 H3C C C NH 2
H3C C
OH H O
H2
H3C C C
H2 H3C CH CH 3
H3C C CH3 OH

H2 H2
H3C C C Cl
or
H O
H3C C CH 3
O H2
H3C C C
Cl H2
O C CH 3
H3C CH 3

O
H2
H3C C C
H
H3C C CH2 Cl

O O
H2 H2
H3C C C O C C CH3
 Task 1. Answers

H2 H2
H3C C C NH2

H2 H2
H3C C C OH
O
O H2
H2 H3C C C NH 2
H3C C
OH H O
H2
H3C C C
H2 H3C CH CH 3
H3C C CH3 OH

H2 H2
H3C C C Cl
or
H O
H3C C CH 3
O H2
H3C C C
Cl H2
O C CH 3
H3C CH 3

O
H2
H3C C C
H
H3C C CH2 Cl

O O
H2 H2
H3C C C O C C CH3
 Task 2. Write the correct names alongside the structures
H2 H2
H3C C C NH2

O
H2 H2
H3C C C OH H2
H3C C C NH 2
O
H2
H3C C
OH
H O
H2
H3C C C
H2 H3C CH CH 3
H3C C CH3 OH

H2 H2
H3C C C Cl
or
H O
H3C C CH 3
O H2
H3C C C
Cl H2
O C CH 3
H3C CH 3

O
H2
H3C C C
H
H3C C CH2 Cl

O O
H2 H2
H3C C C O C C CH3
 Task 2. Answers

propylamine propanenitrile

H2 H2
H3C C C NH2

propan-1-ol
propanamide
H2 H2
H3C C C OH O
propanal
O H2
H2 H3C C C NH 2
H3C C
propan-2-ol propanoic acid
propane H
OH
O
H3C CH CH 3 H2
H3C C C
H2
H3C C CH3 OH

chloropropane ethyl propanoate

H2 H2
H3C C C Cl
propanone O
or H2
H O H3C C C
H3C C CH 3
H2
O C CH 3
Cl
H3C CH 3 propanoyl chloride
propene O
H2
H3C C C

Cl
H
H3C C CH2
propanoic acid anhydride
O O
H2 H2
H3C C C O C C CH3
 Task 3. Label all arrows with reagents and conditions
H2 H2
H3C C C NH2

H2 H2
H3C C C OH O
O H2
H2 H3C C C NH 2
H3C C
OH H O
H2
H3C C C
H3C CH CH 3
H2 OH
H3C C CH3

H2 H2
H3C C C Cl
or
H O
H3C C CH 3
O H2
H3C C C
Cl H2
O C CH 3
H3C CH 3

O
H2
H3C C C
H
H3C C CH2 Cl

O O
H2 H2
H3C C C O C C CH3
Task 4. Draw in arrows for all the reactions you have met and label with reagents and
conditions. Use a red colour to show oxidations and a blue colour for reductions
H2 H2
H3C C C NH2

H2 H2 O
H3C C C OH
H2
O H3C C C NH 2
H2
H3C C
OH
H

H3C CH CH 3 O
H2 H2
H3C C CH3 H3C C C

OH

H2 H2
H3C C C Cl
or
H O
H3C C CH 3
O H2
H3C C C
Cl H2
O C CH 3
H3C CH 3

O
H2
H3C C C
H
H3C C CH2 Cl

O O
H2 H2
H3C C C O C C CH3
 Tasks 3 and 4. Answers
H2 H2 H2 Nickel
H3C C C NH2 catalyst

H2O / HCl
K2Cr2O7 / cold
NH3 H2SO4 distil
H2 H2 H2O / HCl
H3C C C OH off product heat
O
K2Cr2O7 /
O H2SO4 H2
H2 H3C C C NH 2
H3C C reflux
OH H O
H2O / NaOH H2
H3C C C
H2 H3C CH CH 3
H3C C CH3 1. LiAlH4 (ether) OH
2. H2O

Ethanol /
K2Cr2O7 /
H2 H2 H2SO4 reflux
H3C C C Cl H2SO4 reflux
or NH3
SOCl2 H O H2O
H3C C CH 3
O H2
H3C C C
Cl H2
O C CH 3
H2O / KOH in H3C CH 3
Al2O3 heat H2SO4 ethanol ethanol
heat
O
HCl 1. LiAlH4 (ether) H2
2. H2O H3C C C
H2 Nickel
H H2O / H2SO4
catalyst H3C C CH2 Cl

Ethanol /
H2SO4 reflux
addition or
elimination substitution O O
H2 H2
H3C C C O C C CH3
oxidation reduction