VimalSKatiyar_Chemistry_Organic_

ALKENES_EliminationRxns

Saturday, 26 November 2016

ELIMINATION REACTIONS [ALKYL HALIDES AND ALKENES]

1. What alkyl halide forms each of the following alkenes as the only product in an elimination reaction?

2. Which double bonds in the following natural products can exhibit stereoisomerism? Farnesene is found in the
waxy coating of apple skins and geranial is isolated from lemon grass.

3. Label each pair of alkenes as constitutional isomers, stereoisomers, or identical.

PGF2 is a prostaglandin, a compounds responsible for inflammation.

(a) How many tetrahedral stereogenic centers does PGF2 contain?

(b) How many double bonds can exist as cis and trans isomers?

(c) Considering both double bonds and tetrahedral stereogenic centers, what is the maximum number of
stereoisomers that can exist for PGF2?

5. Rank the alkenes in each group in order of increasing stability.

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ALKENES_EliminationRxns

Saturday, 26 November 2016

6. H values obtained for a series of similar reactions are one set of experimental data used to determine the
relative stability of alkenes. Explain how the following data suggest that cis-2-butene is more stable than 1butene.

7. Draw all constitutional isomers formed in each E2 reaction; predict the major product using the Zaitsev rule.

8. Consider the following E2 reaction:

a. Draw the by-products of the reaction and use curved arrows to show the movement of electrons.

b. What happens to the reaction rate with each of the following changes:

i) The solvent is changed to DMF.

ii) The concentration of OC(CH3)3 is decreased.

iii) The base is changed to OH.

iv) The halide is changed to

v) The leaving group is changed to I .

CH3CH2CH2CH2CH(Br )CH3

9. Dehydrohalogenation of 1-chloro-1-methylcyclopropane affords two alkenes (A and B) as products. Explain why

A is the major product despite the fact that it contains the less substituted double bond.

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ALKENES_EliminationRxns

Saturday, 26 November 2016

10. Draw all constitutional isomers formed in each elimination reaction. Label the mechanism as E2 or E1.

11. Which elimination reaction in each pair is faster?

12. Explain the following observation. Treatment of alkyl chloride A with NaOCH2CH3 yields only one product B,
whereas treatment of A with very dilute base in CH3CH2OH yields a mixture of alkenes B and C, with C
predominating.

13. What is the major E2 elimination product formed from each halide?

14. Taking into account anti periplanar geometry, predict the major E2 product formed from each starting material.

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ALKENES_EliminationRxns

Saturday, 26 November 2016

15. The following reactions do not afford the major product that is given. Explain why this is so, and draw the
structure of the major product actually formed.

16. Draw a stepwise, detailed mechanism for the following reaction.

17. Draw a stepwise detailed mechanism that illustrates how four organic products are formed in the following
reaction.

18. Although there are nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane[one of these being gammexane,
the potent insecticide], one stereoisomer reacts 7000 times more slowly than any of the others in an E2
elimination. Draw the structure of this isomer and explain why this is so.
19. Explain the selectivity observed in the following reactions.

20. Although dehydrohalogenation occurs with anti-periplanar geometry, some eliminations have syn-periplanar
geometry. Examine the starting material and product of each elimination and state whether the elimination
occurs with syn or anti periplanar geometry.

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