Return to Contents Chapter 6 : Reactions of Alkenes : Addition Reactions Ch 6 contents
Addition Questions
Qu 1:  Show the major products, with stereochemistry where applicable, for the reactions of :

(a) propene and (b) methylcyclohexene with each of the following : 
(i) H2 / Pd 
(iii) HBr / H2O2
(v) BH3 then NaOH / H2O2
(vii) Cl2 / H2
(ix) O3 then Zn / CH3CO2H
(ii) HBr / dark / N2 atmosphere 
(iv) aq. H2SO4
(vi) Cl2
(viii) CH3CO3

Qu 2: Using diagrams, mechanisms with curly arrows, and / or short paragraphs, explain the following observation:

Qu 3: The following paragaraph describes a series of reactions on a series of unknown but related compounds:

An achiral hydrocarbon A was analysed by combustion analysis. 0.01g of A gave 0.03217g of CO2 and 0.011g H2O. 

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).
In terms of stability (based on heats of combustion), C > B > D

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 - ?
Suggest why and how the A converts to B and C.

Answers ?

organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary