Question

Orgo II Tutorial: Hydroxide Reactions Overview

Answer 1

we will be starting with 1-butanol and going through sevearl synthesis methods

Answer 2

adding a very strong base like NaH will remove the proton from the end. sometimes this can be written with the oxygen anion or with Na+ bonded to it.

Answer 3

now, adding CH3CH2Br

the Br acts as a LG while the oxygen attacks the alkane part
(Williamson ether synthesis)

Answer 4

now let's go back to the initial product

adding MsCl + pyridine replaces the H with a SO2CH3 (note: both of the chlorines are removed as LG's) to gives us:

Answer 5

adding MeONa, the MeO attacks the spot previously occupied by the SO2CH3

Answer 6

going back to the initial product, adding TsCl replaces the H with a Ts (tosylate) group

Answer 7

adding KI replaces the entire OTs group with an iodine atom

Answer 8

adding H2SO4 at high temperatures yields elimination (remember, can somewhat favor substitution at lower temperatures)

Answer 9

same logic w/ SOCl2 except it replaces with Cl instead of Br

Answer 10

adding HBr undergoes SN2 and forms primary bromide

Answer 11

Anyway, that's the end of my tutorial, I hope it was a helpful resource. Source material is Organic Chemistry 12th edition by Solomons, et. al.

Answer 12

nicely done! *claps*