Notes on Alcohols, Phenols, Ethers and Epoxides
Alcohols, ROH
1. There are three classes of alcohols: primary (1°), secondary (2°) and tertiary (3°). Review.
2. Compared with hydrocarbons of same molecular weight, alcohols have higher boiling points
because of hydrogen bonding.
3. The following are some preparation of alcohols that we have already encountered (REVIEW!!!!):
a. Reduction (using NaBH4) of aldehydes into 1° ROH
b. Reduction (using NaBH4) of ketones into 2° ROH
c. Addition of Grignard reagent, RMgX, to formaldehyde (and subsequent subsequent
hydrolysis) to give 1° ROH. The carbon length in addition to one carbon in formaldehyde is
increased, depending on the R in the Grignard reagent.
d. Addition of Grignard reagent, RMgX, to higher aldehydes (and subsequent subsequent
hydrolysis) to give 2° ROH. The carbon length is increased, depending on the R in the
Grignard reagent and the number of carbons in the aldehyde.
e. Addition of Grignard reagent, RMgX, to higher ketones (and subsequent subsequent
hydrolysis) to give 3° ROH. The carbon length is increased, depending on the R in the
Grignard reagent and the number of carbons in the ketone.
f. Hydrolysis of esters into alcohols and carboxylic acids.
g. Reaction of alcohols with HX (=HCl, HBr, HI). However, the reaction works best with 3°ROH.
1° and 2° ROH react very slowly and must be at higher temperatures.
4. The following are some reactions of alcohols that we have already studied:
a. The dehydration of alcohols (elimination of water) to give alkenes
b. The dehydrohalogenation of RX (elimination of HX) to give alkenes
For a) and b), please be mindful of Saytzeff’s rule
c. Preparation of esters (with carboxylic acids, with acid chlorides)
d. Conversion of alcohols into RX. 3°ROH can be converted to RX by either HCl or HBr. 1° and
2° ROH Can be converted to RX by using SOCl2 or PBr3.
e. Oxidation of 1° ROH with K2Cr2O7, H2SO4 gives aldehydes.
f. Oxidation of 1° ROH with KMnO4 gives directly carboxylic acids.
g. Oxidation of 2° ROH with either K2Cr2O7, H2SO4 or KMnO4 gives ketones.
Alcohols, ROH
1. There are three classes of alcohols: primary (1°), secondary (2°) and tertiary (3°). Review.
2. Compared with hydrocarbons of same molecular weight, alcohols have higher boiling points
because of hydrogen bonding.
3. The following are some preparation of alcohols that we have already encountered (REVIEW!!!!):
a. Reduction (using NaBH4) of aldehydes into 1° ROH
b. Reduction (using NaBH4) of ketones into 2° ROH
c. Addition of Grignard reagent, RMgX, to formaldehyde (and subsequent subsequent
hydrolysis) to give 1° ROH. The carbon length in addition to one carbon in formaldehyde is
increased, depending on the R in the Grignard reagent.
d. Addition of Grignard reagent, RMgX, to higher aldehydes (and subsequent subsequent
hydrolysis) to give 2° ROH. The carbon length is increased, depending on the R in the
Grignard reagent and the number of carbons in the aldehyde.
e. Addition of Grignard reagent, RMgX, to higher ketones (and subsequent subsequent
hydrolysis) to give 3° ROH. The carbon length is increased, depending on the R in the
Grignard reagent and the number of carbons in the ketone.
f. Hydrolysis of esters into alcohols and carboxylic acids.
g. Reaction of alcohols with HX (=HCl, HBr, HI). However, the reaction works best with 3°ROH.
1° and 2° ROH react very slowly and must be at higher temperatures.
4. The following are some reactions of alcohols that we have already studied:
a. The dehydration of alcohols (elimination of water) to give alkenes
b. The dehydrohalogenation of RX (elimination of HX) to give alkenes
For a) and b), please be mindful of Saytzeff’s rule
c. Preparation of esters (with carboxylic acids, with acid chlorides)
d. Conversion of alcohols into RX. 3°ROH can be converted to RX by either HCl or HBr. 1° and
2° ROH Can be converted to RX by using SOCl2 or PBr3.
e. Oxidation of 1° ROH with K2Cr2O7, H2SO4 gives aldehydes.
f. Oxidation of 1° ROH with KMnO4 gives directly carboxylic acids.
g. Oxidation of 2° ROH with either K2Cr2O7, H2SO4 or KMnO4 gives ketones.
