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Adiolisa Containing Two (-OH Groups) .: Chemical Compound Hydroxyl Groups

The document discusses several methods for synthesizing alcohols industrially and through reaction chemistry. Methanol is produced industrially from carbon monoxide and hydrogen via synthesis gas. Ethanol can be produced by fermentation of sugars or acid-catalyzed hydration of ethene. Alcohols may also be prepared from haloalkanes by nucleophilic substitution, though side reactions can interfere. Additionally, alcohols can be formed by reducing carbonyl groups, as aldehydes and ketones can be reduced to primary and secondary alcohols, respectively, using hydride reagents like lithium aluminum hydride.

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67 views

Adiolisa Containing Two (-OH Groups) .: Chemical Compound Hydroxyl Groups

The document discusses several methods for synthesizing alcohols industrially and through reaction chemistry. Methanol is produced industrially from carbon monoxide and hydrogen via synthesis gas. Ethanol can be produced by fermentation of sugars or acid-catalyzed hydration of ethene. Alcohols may also be prepared from haloalkanes by nucleophilic substitution, though side reactions can interfere. Additionally, alcohols can be formed by reducing carbonyl groups, as aldehydes and ketones can be reduced to primary and secondary alcohols, respectively, using hydride reagents like lithium aluminum hydride.

Uploaded by

leti332
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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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

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