Bài tập chương 2: PHẢN ỨNG TÁCH

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7. 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.

8.

9. For each of the following reactions, identify whether you would use hydroxide or tertbutoxide to
accomplish the desired transformation:

10. Identify the major and minor products for the E2 reaction that occurs when each of the following
substrates is treated with a strong base:

11. Compound A and compound B are constitutional isomers with the molecular formula C3H7Cl.
When compound A is treated with sodium methoxide, a substitution reaction predominates. When
compound B is treated with sodium methoxide, an elimination reaction predominates. Propose
structures for compounds A and B.
12. Compound A and compound B are constitutional isomers with the molecular formula C4H9Cl.
Treatment of compound A with sodium methoxide gives trans-2-butene as the major product, while
treatment of compound B with sodium methoxide gives a different disubstituted alkene as the major
product.
(a) Draw the structure of compound A.
(b) Draw the structure of compound B
13. An unknown compound with the molecular formula C6H13Cl is treated with sodium ethoxide to
produce 2,3-dimethyl-2-butene as the major product. Identify the structure of the unknown compound.
14. Draw a plausible mechanism for each of the following transformations:

15. Draw all constitutional isomers with the molecular formula C4H9Br, and then arrange them in
order of:

16. Propose the structures of all the isomeric alkyl chlrodies having the molecular formula C 5H11Cl.
Identify:
(a) Which isomer undergoes SN1 reaction at the fastest rate?
(b) Which isomer is incapable of reacting by the E2 mechanism?
(c) Which isomer will yield only a single alkene on E2 elimination?
(d) For which isomer does E2 elimination give two alkenes that are not constitutional isomers?
(e) Which isomer yields the most complex mixture of alkenes on E2 elimination?