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Advanced Level Organic Chemistry: Reaction of alcohols with Na, RCOCl and RCOOH

Part 4A. The chemistry of ALCOHOLS

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Part 4.6A Miscellaneous important reactions of alcohols

Sub-index for this page

4.6.1 Reaction with metallic sodium

4.6.2 Reaction with carboxylic acids to form esters

4.6.3 Reaction with acid chlorides to form esters

INDEX of notes on ALCOHOLS chemistry

All Advanced Organic Chemistry Notes

Index of GCSE/IGCSE Oil - Useful Products Chemistry Revision Notes

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4.6.1 Reaction of alcohols with metallic sodium

Alcohols react with metallic sodium to form hydrogen and a solution of an alkoxide ionic salt

(i) alcohol  +  sodium  ===> an alkoxide  +  hydrogen gas

Normal 'hydrogen' gas fizzing is observed at a moderate rate, and the salt product is soluble in the alcohol itself e.g.

ethanol  +  sodium  ===>  sodium ethoxide  +  hydrogen

 2CH3CH2OH + 2Na ===> 2CH3CH2ONa+ +  H2 

There is some similarity with the reaction of sodium with water (Alkali Metals chemistry) and with a non-aqueous liquid acid like ethanoic acid.

(ii) sodium + water ==> sodium hydroxide + hydrogen

2Na + 2H2O ===> 2Na+OH + H2

(iii) sodium  + ethanoic acid  ===>  sodium ethanoate  +  hydrogen

 2CH3COOH + 2Na ===> 2CH3COONa+ +  H2 

All three reactions give hydrogen gas, though the sodium reacts very fast with water and pretty fast with pure ethanoic acid.

The ethoxide, hydroxide and ethanoate are similar because on evaporation of the unreacted ethanol, water or acid, a solid white ionic compound is formed.

It can further be noted that relatively 'unreactive' alkanes do not react with sodium.

similarly with other alcohols ...

 (i)  methanol + sodium ===> sodium methoxide + hydrogen

2CH3OH + 2Na ===> 2CH3ONa+ + H2

(iii)  propan-1-ol + sodium ==> sodium propoxide + hydrogen

2CH3CH2CH2OH + 2Na ===> 2CH3CH2CH2ONa+ + H2

(iv)  butan-1-ol + sodium ==> sodium butoxide + hydrogen

2CH3CH2CH2CH2OH + 2Na ===> 2CH3CH2CH2CH2ONa+ + H2

 

When alkoxides are mixed with water, the alkoxide salt is hydrolysed, the alkoxide ion is a strong base and removes  a proton from water.

e.g.   sodium ethoxide  +  water  ===>  ethanol  +  sodium hydroxide

CH3CH2ONa+ +  H2O  ===>  CH3CH2OH  +  Na+  +  OH-

So the final mixture will be very alkaline.


4.6.2 Reaction of alcohols with carboxylic acids to form esters

Esters are another homologous series of organic compounds (dealt with in detail on another page)

e.g.  using a little conc. sulfuric acid catalyst, and refluxing the mixture

(i) Ethyl ethanoate, an ester,  is formed by the reversible reaction of carboxylic acid and an alcohol e.g.

ethanoic acid + ethanol ethyl ethanoate + water

+ + H2O

sometimes more simply written as

CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O

General word equation: carboxylic acid  +  alcohol    ester  +  water

This is a reversible reaction, so does not go to completion. When the equilibrium point is reached, you have also reached the point of maximum yield, and, you get about 2/3 conversion of the acid and alcohol reactants to the ester product.

(ii) butanoic acid  +  butan-1-ol    butyl butanoate  +  water

(c) doc b  +  alcohols and ether structure and naming (c) doc b    (c) doc b  +  H2O

 

(iii) pentanoic acid  +  propan-1-ol    propyl pentanoate  +  water

(c) doc b  +  alcohols and ether structure and naming (c) doc b    (c) doc b  +  H2O

 

Esters are used in perfumes and food flavourings. Lots of details in section 10b. for the ..

Procedure for preparing an ester, uses of esters, details of esters & carboxylic acids

 


4.6.3 Reaction of alcohols with acid chlorides to form esters

This is a nucleophilic addition of an alcohol to acid/acyl chlorides,  subsequent elimination on esterification to give the ester and hydrogen chloride.

(i) ethanoyl chloride + ethanol ==> ethyl ethanoate + hydrogen chloride

(c) doc b + CH3-CH2-OH ===> (c) doc b +  HCl

(ii) ethanoyl chloride + phenol ==> phenyl ethanoate + hydrogen chloride

(c) doc b  +  (c) doc b ===>  (c) doc b +   HCl

(iii) pentanoyl chloride  +  ethanol  ===> ethyl pentanoate  + hydrogen chloride

(c) doc b  +  alcohols and ether structure and naming (c) doc b  ===>  (c) doc b   +  HCl

 

For more on this reaction see advanced organic chemistry notes:

6.7 The susceptibility of carboxylic acid derivatives to nucleophilic attack - relative reactivity and preparation & reactions of acid chlorides with water, alcohols, ammonia, amines & mechanisms

6.8 Esters - preparation, reactions including hydrolysis and transesterification, uses

6.9 Natural esters - triglyceride fats and oils, manufacture of margarine and biodiesel

For mechanism see Esterification of acid chlorides with alcohols to give an ester mechanism


Doc Brown's Advanced Level Chemistry Revision Notes

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INDEX of notes on ALCOHOLS chemistry

 All Advanced Organic Chemistry Notes

 Index of GCSE/IGCSE Oil - Useful Products Chemistry Revision Notes

 

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