ALCOHOLS AND PHENOLS

ALCOHOLS AND PHENOLS

✓Organic derivatives of water

ALCOHOLS

✓Classified as PRIMARY, SECONDARY, or TERTIARY

depending on the number of organic groups
bonded to the hydroxyl-bearing carbon.
NAMING ALCOHOLS
 NAMING ALCOHOLS

1,2-butanediol
3-methyl-2-pentanol

1,3-dimethylcyclopentanol
NAMING ALCOHOLS

2-propen-1-ol
3-buten-2-ol

2-methyl-2-propen-1-ol
NAMING ALCOHOLS
PHENOLS

✓ AROMATIC to refer to
the class of compounds
that contain six-
membered benzene-
like rings with three
double bonds
benzene
SOME AROMATIC COMPOUNDS
NAMING AROMATIC COMPOUNDS

• disubstituted
NAMING AROMATIC COMPOUNDS

• disubstituted
NAMING AROMATIC COMPOUNDS

• More than 2 substituents

NAMING PHENOLS
PRACTICE

Give IUPAC names for the following compounds:

PRACTICE

Draw structures corresponding to the following IUPAC names:

PREPARATION OF ALCOHOLS
HYDRATION OF ALKENES
HYDROXYLATION OF ALKENES
PRACTICE

Predict the
products of the
following
reactions:
REDUCTION OF CARBONYL COMPOUNDS
REDUCTION OF CARBONYL COMPOUNDS
REACTION MECHANISM
REDUCTION OF CARBONYL COMPOUNDS
REDUCTION OF CARBONYL COMPOUNDS
PRACTICE

What carbonyl compounds would you reduce to obtain the

following alcohols?
REACTION OF CARBONYL COMPOUNDS WITH
GRIGNARD REAGENTS
REACTIONS OF ALCOHOLS

Conversion of Alcohols into Alkyl Halides

REACTIONS OF ALCOHOLS

Conversion of Alcohols into Alkyl Halides

REACTIONS OF ALCOHOLS

Dehydration of Alcohols to Yield Alkenes

REACTIONS OF ALCOHOLS

Dehydration of Alcohols to Yield Alkenes

REACTIONS OF ALCOHOLS

Dehydration of Alcohols to Yield Alkenes

REACTIONS OF ALCOHOLS

Dehydration of Alcohols to Yield Alkenes

PRACTICE

What product(s)
would you
expect from
dehydration of
the following
alcohols with
POCl3 in
pyridine?
Indicate the
major product in
each case.
OXIDATION OF ALCOHOLS
OXIDATION OF ALCOHOLS
OXIDATION OF ALCOHOLS
PRACTICE

What products would you expect from oxidation of the following

compounds with CrO3 in aqueous acid? With pyridinium
chlorochromate?
PHENOLS
PHENOLS
REACTIONS OF PHENOLS

Electrophilic Aromatic Substitution Reactions

REACTIONS OF PHENOLS

Oxidation of Phenols: Quinones

SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
A) Reduction of carbonyl compounds
1) Aldehydes
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
A) Reduction of carbonyl compounds
2) Ketones
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
A) Reduction of carbonyl compounds
3) Esters
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
A) Reduction of carbonyl compounds
3) Esters
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
A) Reduction of carbonyl compounds
4) Carboxylic acid
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
B) Grignard addition to carbonyl compounds
1) Formaldehyde
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
B) Grignard addition to carbonyl compounds
2) Aldehydes
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
B) Grignard addition to carbonyl compounds
3) Ketones
SUMMARY OF REACTIONS

SYNTHESIS OF ALCOHOLS
B) Grignard addition to carbonyl compounds
4) Esters
SUMMARY OF REACTIONS

REACTIONS OF ALCOHOLS
A) Dehydration
1) Tertiary alcohols
SUMMARY OF REACTIONS

REACTIONS OF ALCOHOLS
A) Dehydration
2) Secondary and tertiary alcohols
SUMMARY OF REACTIONS

REACTIONS OF ALCOHOLS
B) Oxidation
1) Primary alcohols
SUMMARY OF REACTIONS

REACTIONS OF ALCOHOLS
B) Oxidation
2) Secondary alcohols
SUMMARY OF REACTIONS

REACTIONS OF ALCOHOLS
B) Oxidation
3) Oxidation of phenols to
quinones
END

Prepared by: FMUCarranza

Reference: John McMurry, 2008. Organic Chemistry 7th Edition. Brooks/Cole. Thomson Learning Inc.
USA