Alcohols and Ethers Flashcards
why are alcohols soluble in water
they have the ability to form hydrogen bonds
what causes an alcohol to become less soluble
when they have a long nonpolar carbon chain
can ethers form h-bonds
yes they can but only with water molecules and not with themselves, so they have similar solubilities to alcohols of the same molecular weight
what boiling points do ethers have? is it greater than or less than alcohols
ethers have similar boiling points to hydrocarbons of same M/W
it is less than alcohols because they cannot form H-bonds with themselves
what occurs in an acid catalyzed hydration of an alkene
a alkene will deprotonate a strong acid (Markovnikov), form a carbocation, and then undergo nucleophilic substitution and then the water will be deprotonated into an alcohol and reform the original acid
what occurs in oxymercuration demercuration
markovnikov addition, anti stereo selectivity via SN2, with 1) Hg(OAC)2, H20 and 2) NaBH4
what occurs in hydroboration oxidation, what are the reagents?
formation of an alcohol via syn addition with anti markovnikov addition with 1) BH3*THF and 2) H2O2, NaOH
what is a feature of Oxygen in an OH group
it is nucleophilic and weakly basic
what is a feature of Hydrogen in an OH group
it is weakly acidic
how can an OH group become a good leaving group
it can be protonated to form H20 which is a better leaving group
what is a hydrogen halide reaction with a 3 alcohol
an OH group will deprotonate a hydrogen halide , form h20 as a leaving group, the h20 will leave, and then the halide ion will attack the carbocation
what do we use to quicken a hydrogen halide reaction with HCl
we use ZnCl2
what occurs when a 1° or a 2° alcohol reacts with PBr3
an alkyl bromide forms with an inversion of stereochemistry (SN2)
what occurs when SOCl2 reacts with a 1° and 2° alcohol
the formation of an alkyl chloride with an inversion in stereochemistry
how does a 2° or 3° alcohol react with HBr
it forms a racemic mixture of an alkyl halide through an SN1 mechanism
