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Q.

The following bimolecular elimination reaction (E2) is carried out with different halogen leaving groups. The per cent yield of the two products (2-hexene and 1-hexene) for each leaving group is listed below.

Question Image
Leaving groupConj. Acid pKa%-yield of 2-hexene%-yield of 1- hexene
X = I-1081%19%
X = Br-972%28%
X = CI-767%33%
X = F3.230%70%

Which of the following statement is (are) true concerning this series of E2 reactions ?

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a

Based on the pKa's of the conjugate acid, I- is the best leaving group and F- is the poorest leaving group

b

When I-, Br- and Cl- are used as leaving groups, Zaitsev's rule is followed

c

F- is the strongest base (and therefore the poorest leaving group) and the transition state for reaction with fluoride as the leaving group has the least double bond character

d

a, b, c are true

answer is D.

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Detailed Solution

A good leaving group is that which can be removed or displaced very easily.

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The following bimolecular elimination reaction (E2) is carried out with different halogen leaving groups. The per cent yield of the two products (2-hexene and 1-hexene) for each leaving group is listed below.Leaving groupConj. Acid pKa%-yield of 2-hexene%-yield of 1- hexeneX = I-1081%19%X = Br-972%28%X = CI-767%33%X = F3.230%70%Which of the following statement is (are) true concerning this series of E2 reactions ?