Alkenes Summary

1. Structural isomerism: branching or different position of the C=C.

2. Cis-trans isomerism is present in alkenes due to C=C bond. (recall: conditions for
cis-trans isomerism to be exhibited)
3. Boiling point of alkenes are low, and increases with increasing number of C. (recall:
increasing strength of id-id attractions)
4. Soluble in non-polar solvents, not soluble in polar ones. (recall: energy released
when interactions are formed vs energy taken in when existing interactions are
broken.)
5. Cis-isomers have higher boiling points than trans-isomers, due to net dipole
moment, hence presence of pd-pd attractions. (recall: pd-pd > id-id)
6. For elimination reactions (usually preparation of alkenes), the more substituted
alkene will be the more stable product.
7. For addition reactions, the more electron-donating alkyl groups attached to the C+,
greater extent of dispersal of positive charge on the carbocation, resulting in a more
stable carbocation intermediate formed.
8. When the resulting mixture is optically inactive, it is due to the intermediate having
a trigonal planar structure, allowing an equal probability of attack by the anion from
either side, (+) and (-) enantiomers formed in equal amounts.
9. For oxidation, cold mild oxidation, hot strong oxidation (cleaving of C=C)
10. Methanoic acid and ethanedioic acid undergoes strong oxidation to produce CO2 and
H2O. This is useful for elucidation questions where the loss of C is involved.
11. Steps to draw:
Forward Reverse*
1. Break C=C Draw O=C- -C=O
2. Add =O to C Draw O=C-
3. Add 1 O to H If there is CO2, replace with methanoic
acid
Remove all O and join all C=C bonds
12. Draw the mechanism below:
Practice Question:
(a) Draw the structures of the intermediates and the final products formed when but-2-
ene reacts with
(i) Steam, using phosphoric acid catalyst,
(ii) Bromine in an organic solvent, followed by hot ethanolic KOH,
(iii) Cold, dilute acidified potassium manganate (VII)
(b) An alkene A reacts with hot concentrated potassium manganite (VII) to give the two
acids CH3CO2H (B) and CH3CH2CO2H (C) in equimolar amounts.
(i) Suggest the structural formula of alkene A.
(ii) Acids B and C can be made from ethanol by the routes shown. Suggest a
structure for D, and suggest suitable reagents and conditions for reactions I,
II, III and IV.
C2H5OH (I) CH3CO2H (B)
(II)
D (III) CH3CH2CN (IV) CH3CH2CO2H
(C)