SCH4U
ORGANIC CHEMISTRY
ANSWERS
The shortest pathway is shown for the answers, this does not mean that it is the only pathway. Be sure you have
named all the organic materials at least once.
1. Use ethane to produce hexane.
HF
+
ethane
F
HF
+
F
F
+
F
fluoroethane
butane
HF
hexane
2. Use ethane to produce ethoxybutane.
F
+
F
F
HF
HF
+
ethane
fluoroethane
butane
HF
+
F
F
+ H2O
F
HF
OH
butan-1-ol
F
+ H2O
H2O
OH
HF
O
+
OH
ethoxybutane
ethanol
3. Use but-2-ene to produce butan-2-one.
O
OH
+
+
H2O
(O)
H2O
butan-2-one
butan-2-ol
but-2-ene
4. Use propane to produce 2-chloropropene.
Cl
Cl
propane
+
Cl
Cl
+
HCl
2-chloropropane
H2
2-chloroprop-1-ene
5. Use pent-1-en-3-one to produce pentane.
Note: The reverse of oxidation is called reduction.
O
O
+
OH
(O)
H2O
H2
pentan-3-one
pent-1-en-3-one
pentane
pentan-3-ol
6. Use butane and methane to produce 2-methylbutan-1-ol.
CH4
+
HF
F
F
HF
+
fluoromethane
methane
HCl
F
Cl
+ H2O
1-chloro-2-methylbutane
butane
HCl
+
2-methylbutane
HO
2-methylbutan-1-ol
Cl
Cl
SCH4U
ORGANIC CHEMISTRY
ANSWERS
7. Use ethylpropanoate to produce ethene and propane.
O
O
+
O
H2O
+
OH
ethyl propanoate
H2O
H2
OH
ethane
O
HO
propanoic acid
ethanol
ethene
OH
2(O)
H2O
HO
propane
propan-1-ol
8. Use benzene to produce phenol.
OH
Cl
HCl
+
Cl
+ H2O
Cl
HCl
phenol
chlorobenzene
benzene
9. Use methane to produce N-methylethanamine.
CH4
+
HBr
Br Br
+
Br
HBr
CH4
bromomethane
methane
HCl
NH2
+
+
ethane
Cl
HCl
Cl
Cl
chloroethane
HBr
Br
NH
ethanamine
N-methylethanamine
10. Produce N-butyl-N-ethylhexanamine from a single organic molecule.
+
HBr
Br Br
Br
ethane
Br
bromoethane
HBr
+
HBr
+
Br
butane
+
Cl
hexane
HCl
Cl
Cl
1-chlorobutane
+
F
F
HF
F
1-fluorohexane
Br
+
NH3
HCl
HBr
NH2
+
Cl
NH
N-ethylbutan-1-amine
ethanamine
NH
+
+
HF
N
F
N-butyl-N-ethylhexan-1-amine
NH3
SCH4U
ORGANIC CHEMISTRY
ANSWERS
11. Use any straight chain organic molecules you wish to produce 1-ethyl-3-methylcyclohexane.
+F
HF
HF
F
F
1-fluorohexane
hexane
+
cyclohexane
HCl
ethene
HCl
+
Cl
chloroethane
ethylcyclohexane
CH4
+
F
HF
HF
F
F
+
fluoromethane
methane
1-ethyl-3-methylcyclohexane
12. Use propane to produce a triglyceride where the fatty acid chains are each six carbons long. (Tricky!)
+
F
HF
F
F
propane
+
Cl
HF
+
hexane
HCl
Cl
Cl
+
HCl
H2O
OH
hexan-1-ol
1-chlorohexane
O
+ 2(O)
2 H2O
OH
hexanoic acid
F
+
3F
HF
F 3
F
F
+ 3 H2O
OH
3 HF
HO
propane-1,2,3-triol
1,2,3-trifluoropropane
O
3
OH
OH
+ HO
OH
OH
O
3 H2O
O
O
O
O
triglyceride
O
Show the polymerization of the following molecules, using four monomers unless otherwise stated.
1. Monomer 2-methylbutan-1,4-diol.
HO
OH
+
HO
OH
+ HO
OH
+
HO
OH
2-methylbutane-1,4-diol
3 H2O
HO
O
O
OH
O
poly[2-methylbutane-1,4-diol]
SCH4U
ORGANIC CHEMISTRY
ANSWERS
2. Alternate propan-1,3-diol with ethandioic acid.
O
+
OH
HO
O
OH
HO
propane-1,3-diol
+
OH
HO
O
O
O
ethanedioic acid
O
O
HO
3 H2O
OH
+ HO
O
O
OH
O
poly[propan-1,3-diol, ethandioic acid]
O
3. Monomer 2-chloropent-1-ene.
Cl
Cl
Cl
Cl
+
+
+
2-chloropent-1-ene
Cl
Cl
poly[2-chloropent-1-ene]
Cl
Cl
4. Alternate 1,2-diaminethane with 1,4-dihydroxybenzene.
H2N
NH2
+
HO
+
1,2-diaminoethane
H2N
NH2
+
HO
OH
OH
1,4-dihydroxybenzene
NH
H2N
NH
NH
poly[1,2-diaminoethane, 1,4-dihydroxybenzene]
NH
NH2
SCH4U
ORGANIC CHEMISTRY
ANSWERS
5. Show the polymerization of the nine essential amino acids in alphabetical order. (Tricky!)
The nine essential amino acids are: histidine, isoleucine, leucine, lysine, methionine, phenylalanine,
threonine, tryptophan, and valine. They bond using an amide linkage between the carboxylic acid on
one amino acid with the amine on the other acid. This produces a water molecule for each link formed,
for a total of eight in this process. Here the amino acids are bonded together in alphabetical order.
O
N
N
H
O
+
OH
O
+
HO
NH2
OH
NH2
histidine
isoleucine
OH
H2N
leucine
+
O
OH
+
HO
OH
NH2
NH2
NH2
phenylalanine
O
OH
lysine
O
S
methionine
+
NH2
O
+
O
threonine
O
OH
+
+
NH2
NH
OH
8 H2O
NH2
valine
tryptophan
NH2
O
N
N
H
NH
NH2
O
NH
HO
O
NH
O
O
O
NH
NH
NH
S
NH
O
NH
O
HN
OH
O
NH2