Answer scheme of tutorial Chapter 3b – Alkene & Alkyne

1. a) (2Z, 4E, 6E)-4,5-dichloro-3,6-dimethylocta-2,4,6-triene

b) (2E)-2-bromo-3-(bromomethyl)pent-2-ene
c) (4Z)-3-chlorohept-4-en-1-yne
d) (1Z, 7E)-1,8-dichloroocta-1,7-dien-4-yne

2. a) Trans-2-pentene is more stable because it has less steric strain than the cis-2-pentene.
b) Trans-2,2,5,5-tetramethyl-3-hexene is more stable than cis-2,2,5,5-tetramethyl-3-
hexene due to lesser steric strain.
The least stable compound would be cis-2,2,5,5-tetramethyl-3-hexene of all compounds
because it has both tert-butyl groups on the same side which increase the steric effect.

3. a) D.O.U = (18 – 14)/ 2 = 2

b) D.O.U = (22 – 18)/2 = 2
c) D.O.U = (56 – 46)/ 2 = 5
d) D.O.U = (30 – 14)/ 2 = 8

4.
a)

b)

c)

d)

e)
 f)

5. Saturated C8 has 18 Hs, thus:

D.O.U = (18 – 10)/2 = 4

Since one equivalent of H2 is absorbed over the Lindlar’s catalyst, one triple bond is
present.
Hydrogenation over Pd catalyst absorbed 3 equivalent H2, two from the triple bond, thus
one double bond must be present.
The structure must contain one ring to account for one more degree of unsaturation.
Possible structure (but not limited to only these structures):

6.