Give the mechanism and major product for the reaction of a secondary haloalkane in a polar aprotic

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Give the mechanism and major product for the reaction of a secondary haloalkane in a polar aprotic solvent with the following nucleophiles. The pKa value of the conjugate acid of the nucleophile is given in parentheses.
(a) N3- (4.6)
(b) H2N- (35)
(c) NH3 (9.5)
(d) HSe- (3.7)
(e) F- (3.2)
(f) C6H5O- (9.9)
(g) PH3 (-12)
(h) NH2OH (6.0)
(i) NCS- (-0.7)
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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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