Marked answers are given in red.
Q1
| Wrong name | IUPAC name |
| 2-ethylpentane | 3-methylhexane |
| 3-isopropylpentane | 3-ethyl-2-methylpentane |
| 2-methyl-2-hydroxybutane | 2-methylbutan-2-ol |
| hepta-3,6-diyne | hepta-1,4-diyne |
| 4-bromo-5-isopropylnona-1-yne-trans-7-ene | (E)-6-bromo-5-isopropylnon-8-yne-2-ene |
| 3-oxopentan-1-ol | 1-hydroxypentan-3-one |
| 5-oxopentan-1-ol | 5-hydroxypentanal |
| 5-chloropentane | 1-chloropentane |
| 3-methyl-5-ethyloctane | 5-ethyl-3-methyloctane |
| 1-chloropropan-3-oic acid | 3-chloroprpanoic acid |
| trans-1-chloro-1-bromocyclopentane | 1-bromo-1-chlorocyclopentane |
| 5-hydroxy-5-methyl-8-oxooctan-3-one | 4-hydroxy-4-methyl-6-oxooctanal |
| heptan-4-yne | heptan-3-yne |
| trans-2-methylhexan-5-ene | 5-methylhex-1-ene |
| cis-4,6-dimethylcyclohexanone | cis-2,4-dimethylcyclohexanone |
| 1-iodo-2-chlor-3-fluoro-4-bromohex-5-ene | 3-bromo-5-chloro-4-fluoro-6-iodohex-1-ene |
| hexa-1,6-dioic acid | hexanedioic acid |
| sodium 3-bromo-2-iodo-3-ethyl-2-butyldecan-6,8-dienoate | sodium 3-bromo-2-butyl-3-ethyl-2-iododecan-6,8-dienoate |
Q2
From top left, across the page:
2,4-dimethylhexane
(Z)-6,6-dimethyloct-2-ene
10-hydroxy-4-methyldecanal
propanedioic acid
2-brombutanoic acid
From bottom left, across the page:
1,1,1-trifluoropropanone
trans-1,2-diethylcyclohexane
1-isopropylcyclopentene
4-cycloheptyl-7-cyclopropyl-6-methyl-5-propyloct-1-ene
(Z)-5-ethyl-2,4-dimethylhepta-4,6-dien-3-one
Q3.1
a. A major driving force introduced in this class is the reaction of an electron rich centre with an electron poor centre.
b. Haloalkanes have an electron deficient carbon centre due to the polarization of the C - Halogen bond. Any group reacting with a haloalkane needs to be electron rich. CN- is electron rich and so will react. H+ is electron poor and so will not react.
c. The p bond of an alkene is electron rich and will react readily with electron poor centres.NO+ is electron poor and so will react. NO2- is electron rich and so will not react.
Q3.2
a. haloalkane to alkanol: use hydroxide ion.
b. a secondary alkanol can be oxidized with KMnO4 to give an alkanone.
c. An alkanone can be reduced to an alkanol using LAH followed by a water work up.
d. An alkanal can be oxidized to an alkanoic acid with KMnO4.
e. An alkene will add HCl to give a chloroalkane.
f. An alkyne can be reduced using Hydrogen gas with a Platinum catalyst to gave an alkane.
g. A primary haloalkane can be converted into an alkanoic acid in two steps: first convert the haloalkane into an alkanol using hydroxide ion (as in part (a)); second oxidize the primary alkanol to the alkanoic acid with KMnO4.
h. A secondary alkanol can be converted into an oxime in two steps: first oxidize the secondary alkanol to an alkanone with KMnO4; second react the alkanone with hydroxylamine to give the oxime.
Q3.3
| reactant 1 | reactant 2 | product | |
|---|---|---|---|
| a | hex-1-yne anion | 1-bromobutane | dec-5-yne |
| b | hex-5-yn-1-ene anion | bromethane | oct-1-en-5-yne |
| c | hex-1-yne anion | propanal | non-4-yn-3-ol |
| d | propyne anion (2 equivs) | propanedial | non-2,7-diyne-4,6-diol |
| e (step 1) | but-1-yne anion | 1-bromopropane | hept-3-yne |
| e (step 2) | hept-3-yne | hydrogen/platinum | heptane |
| f (step 1) | but-1-yne anion | butanal | oct-5-yn-4-ol |
| f (step 2) | oct-5-yn-4-ol | hydrogen/platinum | octan-4-ol |
Q3.4
a. Primary alkanol and alkanal: use 2,4-DNP. Alkanal reacts.
b. Alkene and alkanone: use KMnO4. Alkene reacts
c. Alkanone and alkanal: use KMnO4. Alkanal reacts.
Q4.
Oxidation by KMnO4:
| reactant | product |
|---|---|
| cyclohexene (cold KMnO4 | cis-cyclohexane-1,2-diol |
| 3-methylpentan-3-ol | No reaction (tertiary alkanol) |
| 4-oxopentanal | 4-oxopentanoic acid |
| chlorocyclohexane | No reaction |
| cyclohexanol | cyclohexanone |
Q5.
| reactant | reagent(s) | product | |
|---|---|---|---|
| a | (E)-hex-3-ene | H2 / Pt | hexane |
| b | butanone | 1. LAH; 2. H2O | Butan-2-ol |
| c | (E)-hex-3-ene | HCl | 3-chlorohexane |
| d | butan-1-ol | ZnCl2 / HCl | 1-chlorobutane |
| e | pent-1-yne | Br2 (2 equivs) | 1,1,2,2-tetrabromopentane |
| f | |
|
|
| g | 1-chlorohexane | LAH | hexane |
| h | 1-bromo-3-methylbutane | hydroxide ion | 3-methylbutan-1-ol |
| i | |
NH2OH | |
| j | 1-bromobutane | hex-1-yne anion | dec-5-yne |