Please propose the reagents for converting (R)-butyl alcohol to: A. (S)-2-butyl

Question

Please propose the reagents for converting (R)-butyl alcohol to:
A. (S)-2-butyl chloride
B. (R)-2-butyl bromide
C. (R)-2-butyl azide
D. (R)-2-butane thiol
E. (R)-2-methyl butyronitrile (Butyronitrile is H3CCH2CH2CH2CN).
F. (S)-2-butyl fluoride

I know the reagent for the first one could be HCl, being that the product is stereochemically opposite of the reactant, making it a possible Sn2 reaction. I am just not sure how to narrow it down on the other questions. Any help would be greatly appreciated!

Explanation / Answer

a) HCl b) HBr c) Sodium Azide d) C–SH or R–SH e) NH3 f) HF

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