Exam 1 - Alcohols Flashcards
___, ___, and ___ alcohols can react with sulfonate esters + base.
primary, secondary, and tertiary
The larger the alcohol, the ___ acidic.
less
___ can need heat.
E1
Alcohols reacting with sulfonate esters lead to ___ of stereochemistry in the final product.
retention
Alcohols reacting with PBr3 lead to ___ of stereochemistry in the final product.
inversion
___, ___, and ___ alcohols can react with sulfonate esters.
primary, secondary, tertiary
You can react an alcohol directly with a ___, in order to create an alkoxide.
metal (M = Li, Na, K)
Primary branched alcohols reacting with strong acids can lead to ___ ___.
carbocation rearrangements
SN2/E2 are faster in ___ ___ solvents.
polar aprotic (polar no OH)
The mechanism of alcohols reacting with sulfonate esters also requires ___ in order to deprotonate the LG.
NEt3 (a base)
Two examples of bases used in alcohol reactions:
NEt3 and pyridine
An alcohol reacting with H2SO4 will produce a(n) ___ via an ___ mechanism.
alkene, elimination
An alcohol is a ___ attached to a ___ carbon.
-OH, sp3
E2 needs a ___/___ base.
strong/bulky base
___/___ are faster in polar protic solvents.
SN1/E1
___ and ___ alcohols can react with SOCl2/SOBr2 + base.
primary, secondary
Alcohols reacting with SOCl2 and NEt3 lead to ___ of stereochemistry in the final product.
inversion
Bigger alcohols are less acidic, because it is harder to stabilize the ___ ___.
conjugate base
___, ___, and ___ alcohols can react with H2SO4.
primary, secondary, tertiary
The ___ the alcohol, the less acidic.
larger
Usually the more substituted alkene is favored (___ Rule).
Zaitsev’s Rule
Remember: ___ ___ can happen in SN1 and E1 reactions!
carbocation rearrangements
___ = Deprotonated alcohol.
alkoxide
In alcohols reacting with strong acids (HBr, HI, HCl): ___ reacts faster than ___ which reacts faster than ___.
tertiary, secondary, primary
