Ch 11 Reactions of Alcohols
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dehydration of an alcohol produces what product(s)?
alkenes
oxidation of an alcohol produces what product(s)?
ketones, aldehydes, acids (ex: carboxylic acid)
substitution of an alcohol produces what product(s)?
halides (R-X)
reduction of an alcohol produces what product(s)?
alkanes (R-H)
esterification of an alcohol produces what product(s)?
esters (R-O-C(=O)-R’)
tosylation of an alcohol produces what product(s)?
tosylate esters (R-OTs) (a good leaving group)
deprotination of an alcohol (R-OH) to form an alkoxide and treatment with an alkyl halide (R’-X) produces what product(s)?
ethers (R-O-R’)
give examples of oxidation based on the change of the formula of the substance:
addition of O or O2; addition of X2 (halogens); loss of H2
give examples of reduction based on the change of the formula of the substance:
addition of H2 (or H-); loss of O or O2; loss of X2
give examples of changes in formula of the substance which are condisered neither oxidation nor reduction:
addition or loss of H+, -OH, H2O, HX (more options possible)
what does oxidation normally do in terms of bonded atoms to carbon?
generally converts C-H bonds to C-O bonds
what species is more oxidised, an alkane or a carboxylic acid?
carboxylic acid
what species is more oxidised, an alkane or a ketone?
ketone
what species is more oxidised, an alkane or an aldehyde?
aldehyde
what species is more oxidised, an alkane or a primary alcohol?
primary alcohol
what species is more oxidised, an alkane or a secondary alcohol?
what species is more oxidised, a primary alcohol or an aldehyde?
aldehyde
what species is more oxidised, an aldehyde or a carboxylic acid?
carboxylic acid
what species is more oxidised, a secondary alcohol or a ketone?
ketone
what species is more oxidised, a primary alcohol or a carboxylic acid?
carboxylic acid
classify the groups formed form the oxidation of an alkane from most reduced to most oxidised, starting with a 1° carbon
alkane, primary alcohol, aldehyde, carboxylic acid
classify the groups formed form the oxidation of an alkane from most reduced to most oxidised, starting with a 2° carbon
alkane, secondary alcohol, ketone
classify the groups formed form the oxidation of an alkane from most reduced to most oxidised, starting with a 3° carbon
alkane, tertiary alcohol
what do most alcohol oxidising agents have in common, and how do they work?
all have an element (ex: Cr, Cl, I, S) in a high oxidation state bonded to oxygen. The mechanisms are also similar, the first step an intermediate forms in which the oxidant element becomes bound to the alcohol’s oxygen, and after a base removes a proton from the carbinol carbon atom a double bond forms to oxygen, resulting in a oxydised alcohol (a ketone or aldehyde) and a reduced oxidant.
