Alcohol Reactions

the more substituted an alcohol is, what happens to the solubility

it decreases

primary alcohols are miscible, the more carbons attached then the less will dissolve

which has the highest boiling point: alcohol, aldehyde, ether

alcohol > aldehyde > ether

T or F: tertiary alcohols are the most acidic

false, it is the least acidic

alcohol attached the a methyl is most acidic, then primary, then secondary

if we only want to reduce a ketone, what reagents would we use

NaBH4 or LiAlH4/H3O+

reduction

identify the type of reaction occurring

preparation of alcohols via grinard reagent

what reagent would be used to remove the TMS attached

TBAF would be used to remove TMS, which is a protection group

T or F: S_N1 conditions cannot be used to convert a primary alkyl halide into an alcohol. S_N2 conditions are required for such a transformation.

T

for alcohols, we can do SN2 back side attack on a primary alcohol

if you wanted to replace a primary alcohol with a chlorine in a substitution, we cannot use HCL like we do with HBR. what else do we need

we need ZnCL to be out catalyst so Zn can be a leaving group

if you see PBR3 and pyridine OR SOCl2 and pyridine with an alcohol, what type of reaction are we doing

SN2

we make a PBr2- / SOCL- to serve as a good leaving group so the bromide ion/chloride ion can do backside attack

what reagent would give us E1/E2 of an alcohol

concentrated H2SO4

if i have a primary alcohol and i want to form a carboxylic acid via oxidation, what reagent do i use? what if i want to stop at the aldehyde

chromic acid (H2CrO4)

PCC if you want aldehyde

if i have a secondary alcohol and i do an oxidation reaction (chromic acid or PCC it dont matter) what product will i get

ketone

what product will form via oxidation of a tertiary alcohol

nothing - there won’t be a rxn

if a have a secondary alcohol, but need to do an SN2 reaction, what reagent can i use to prep?

TSCl/pyridine because it will add OTs to same side then you can do backside attacl