Organic Reaction 1
15
Organic reaction maps
Transcript of Organic Reaction 1
Organic reaction maps
propane
chloropropane
propan-2-ol
ethylpropanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
Task 1. Highlight all oxidations red, reductions blue, substitutions green and additions or eliminations yellow
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
Task 1. Answers
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
Task 2. Draw the correct structures alongside the names
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
Task 2. Answers
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3CHC CH2
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
CH3-CH2C=N
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
K2Cr2O7 / H2SO4 reflux
Task 3. Label all arrows with reagents and conditions
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
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid chloride
propanoyl chloride
K2Cr2O7 / H2SO4 reflux
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
K2Cr2O7 / H2SO4 reflux
K2Cr2O7 / H2SO4 distil off product
K2Cr2O7 / H2SO4 reflux
H2O / HCl
heat
H2O / H2SO4
H2O
H2 Nickel catalyst
1. LiAlH4 (ether) 2. H2O
1. LiAlH4 (ether) 2. H2OH2 Nickel
catalyst
Ethanol / H2SO4
reflux
ethanol
Ethanol / H2SO4
reflux
NH3
H2O / HCl
coldNH3
Al2O3 heat
SOCl2
H2O / H2SO4
heat
H2O / NaOH
Tasks 3 and 4. Answers
Addition or elimination
oxidation
substitution
Reduction
HCl
KOH in ethanol
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3C C N
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
Task 1. Highlight all oxidations red, reductions blue, substitutions green and additions or eliminations yellow
H3CHC CH2
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3CHC CH2
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
Task 1. Answers
H3C C N
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3CHC CH2
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3C C N
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
Task 2. Write the correct names alongside the structures
propane
chloropropane
propan-2-ol
ethyl propanoate
propanoic acid
propanamide
propanenitrile
propanone
propanal
propan-1-ol
propylamine
propene
propanoic acid anhydride
propanoyl chloride
Task 2. Answers
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3CHC CH2
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3C C N
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
Task 3. Label all arrows with reagents and conditions
H3CHC CH2
H3C C N
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3CHC CH2
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3C C N
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C 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
K2Cr2O7 / H2SO4 reflux
K2Cr2O7 / H2SO4 distil off product
K2Cr2O7 / H2SO4 reflux
H2O / HCl
heat
H2O / H2SO4
H2O
H2 Nickel catalyst
1. LiAlH4 (ether) 2. H2O
1. LiAlH4 (ether) 2. H2OH2 Nickel
catalyst
Ethanol / H2SO4
reflux
ethanol
Ethanol / H2SO4
reflux
NH3
H2O / HCl
coldNH3
Al2O3 heat
SOCl2
H2O / H2SO4
heat
H2O / NaOH
H3CH2C
H2C Cl
H3CHC CH3
Cl
or
H3CH2C CH3
H3CHC CH2
H3C CH
OH
CH3
H3CH2C
H2C OH
H3CH2C
H2C NH2
H3CH2C
O
H
O
H3C CH3
H3CH2C C NH2
O
H3CH2C C
O
OH
H3CH2C C
O
OH2C CH3
H3CH2C C
O
Cl
H3CH2C C
O
O C
O
H2C CH3
addition or elimination
oxidation
substitution
reduction
Tasks 4. Answers
KOH in ethanol
HCl
CH3-CH2C=N
