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Primary alcohol + Water
Sn2 reaction
requires heat
protonation of -OH group
backside nu attack and LG leaves (HOH)
inversion of stereochemistry
secondary alcohol + water
Sn1 reaction
LG leaves to form carbocation
rearrangement may occur
nu attack (top or bottom)
tertiary alcohol + water
doesnt require heat
possible competing E1 reaction
could then undergo substitution and form substitution product
sulfonate ester synthesis
sulfonyl chloride + alcohol in pyrridine (acts as a solvent and base)
ex: TsCl --> OTs
What is the function of ZnCl in halogenation of alcohols?
is a better activating agent when alcohol reacts with Cl - the weakest nucleophile
helps speed the reaction AND shift equilibrium (make the reaction go to completion by forming more of the alkyl halide)
What is the function of Pyrridine?
halogenation reactions with PBr3/PCl3/SOCl2
synthesis of sulfonate esters
acts as a solvent and a base
how is a sulfonate ester synthesized?
from sulfonyl chloride and alcohol
pyrridine solvent
why sulfonate esters are useful in synthesis
anion makes a good LG (stabilized by delocalized electrons)
ex: -OTs
difference between dehydration with POCl3 (mild) and with H2SO4 (reactive)
mild conditions = E2 reaction
reactive conditions = E1 reaction
formation of carbocation intermediate may or may not change products formed
oxidation with secondary vs primary alcohols (tertiary cannot be oxidized)
secondary --> ketones
primary --> aldehydes
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