8.

4 Industrial Sources of Alcohols: Carbon Monoxide and Ethene

Synthesis gas- pressurized carbon monoxide with hydrogen gas

Methanol production is very cheap via synthesis gas
A diol is a chemical compound containing two hydroxyl groups (OH groups).

Ethanol prepared in large quantities by fermentation of sugars or by

phosphoric acid-catalyzed hydration of ethane.
Summary: The industrial preparation of methanol and 1,2-ethanediol
proceeds by reduction of carbon monoxide with hydrogen. Ethanol is
prepared by fermentation or the acid-catalyzed hydration of ethane
(ethylene).

8.5 Synthesis of Alcohols by Nucleophilic Substitution

Main alcohols we are making are methanol and ethanol (Not addressed in
lecture)
Haloalkanes into alcohols by SN2 and SN1 reactions
o Bimolecular elimination is a major side reaction of hindered systems
and tertiary halides from carbocations that may undergo E1 reactions
Can overcome these issues by using polar, aprotic solvents
Alcohols from Haloalkanes by Acetate Substitution- Hydrolysis

Summary: Alcohols may be prepared from haloalkanes by nucleophilic

substitution, provided the haloalkane is readily available and side reactions
such as elimination do not interfere.

8.6 Synthesis of Alcohols: Oxidation-Reduction Relation Between Alcohols and

Carbonyl Compounds

Oxidation and reduction have special meanings in organic chemistry

o Oxidation- process that adds electronegative atoms suchs as halogen
or oxygen to, ro removes hydrogen from, a molecule
o Reduction- the removal of halogen or oxygen or the addition of
hydrogen
Oxidation of methane to carbon dioxide

Redox reaction Between alcohols and carbonyl compounds

NUCLEOPHILIC ADDITION OF LiAlH 4 TO AN ALDEHYDE

Step 1:
The nucleophilic H in the hydride reagent adds to the
electrophilic C in the polar carbonyl group in the aldehyde,
electrons from the C=Omove to the O creating an
intermediate metal alkoxide complex.
(note that all 4 of the H atoms can react)
Step 2:
This is the work-up step, a simple acid/base reaction.
Protonation of the alkoxide oxygen creates the primary
alcohol product from the intermediate complex.

http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch15/ch15-2-7.html

Alcohols can form by hydride reduction of the barony group

o Polar character of the carbonyl function

http://www.chem.ucla.edu/harding/notes/notes_14D_C=Ofun01.pdf

http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biologic
al_Emphasis/Chapter_12:_Acyl_substitution_reactions/Section_12.4:_Esters

http://web.mnstate.edu/jasperse/Chem350/Handouts/Ch%204%20Stability
%20Reactivity%20(p16-18).pdf

http://www.chem.ucla.edu/harding/notes/notes_14D_C=Ofun01.pdf