| Qu 1: |
Show the major products,
with stereochemistry where applicable, for the reactions of : |
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(a) propene and (b)
1-methylcyclohexene with each of the following :
(i) H2 / Pd
(iii) HBr / H2O2
(v) BH3 then NaOH / H2O2
(vii) Cl2 / H2O
(ix) O3 then Zn / CH3CO2H |
(ii) HBr / dark / N2 atmosphere
(iv) aq. H2SO4
(vi) Cl2
(viii) CH3CO3H |
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| Qu 2: |
Using diagrams, mechanisms
with curved arrows, and / or short paragraphs, explain the following observation: |
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| Qu 3: |
The following paragaraph
describes a series of reactions on a series of unknown but related compounds: |
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An hydrocarbon A
was analyzed by combustion analysis. 0.01g of A gave 0.03217g of
CO2 and 0.011g H2O. |
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A was added
to conc. H2SO4 and the non-polymeric portion of the
organic extract was found to contain small amounts of the starting material
A and three other isomeric hydrocarbons, B, C and D.
All four compounds were further investigated chemically by their reactions
with H2 / Pt and with HBr (dark).
Reaction of either A or D with H2 / Pt gave ethylcyclobutane.
Reaction of A with HBr (dark) gave E, a secondary bromide
whereas reaction of D with HBr (dark) gave F, a tertiary isomer
of E.
Reaction of either B or C with H2 / Pt gave methylcyclopentane.
Reaction of B or C with HBr (dark) gave G.
What are A
- G ?
Suggest why and how the A converts to B and C.
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