HOME PAGE * KS3 SCIENCES * GCSE BIOLOGY  CHEMISTRY  PHYSICS * ADVANCED LEVEL CHEMISTRY

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

AQA Advanced A level Chemistry Edexcel Advanced A level Chemistry OCR Advanced A level Chemistry A OCR Salters Advanced A level Chemistry B

Part 4A. The chemistry of ALCOHOLS

Doc Brown's Chemistry Advanced Level Pre-University Chemistry Revision Study Notes for UK KS5 A/AS GCE IB advanced level organic chemistry students US K12 grade 11 grade 12 organic chemistry

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

[SEARCH BOX]



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


[SEARCH BOX] ignore adverts at top

INDEX of notes on ALCOHOLS chemistry

 All Advanced Organic Chemistry Notes

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

 

KS3 BIOLOGY QUIZZES ~US grades 6-8 KS3 CHEMISTRY QUIZZES ~US grades 6-8 KS3 PHYSICS QUIZZES ~US grades 6-8 HOMEPAGE of Doc Brown's Science Website EMAIL Doc Brown's Science Website
GCSE 9-1 BIOLOGY NOTES GCSE 9-1 CHEMISTRY NOTES and QUIZZES GCSE 9-1 PHYSICS NOTES GCSE 9-1 SCIENCES syllabus-specification help links for biology chemistry physics courses IGCSE & O Level SCIENCES syllabus-specification help links for biology chemistry physics courses
Advanced A/AS Level ORGANIC Chemistry Revision Notes US K12 ~grades 11-12 Advanced A/AS Level INORGANIC Chemistry Revision Notes US K12 ~grades 11-12 Advanced A/AS Level PHYSICAL-THEORETICAL Chemistry Revision Notes US K12 ~grades 11-12 Advanced A/AS Level CHEMISTRY syllabus-specificatio HELP LINKS of my site Doc Brown's Travel Pictures
Website content © Dr Phil Brown 2000+. All copyrights reserved on revision notes, images, quizzes, worksheets etc. Copying of website material is NOT permitted. Exam revision summaries & references to science course specifications are unofficial.

 Doc Brown's Chemistry 

*

best gift deals latest video game release, best gift deals best bargains in shop sales latest pop music releases, best sales deals download free music, latest film releases, best gifts for teenagers latest high street fashion in clothes, fashionable trending in clothing, best gift deals best bargains in shop salesgirls buy clothes, spend a lot of money on clothes, best sales deals shoes, sweets and chocolates, magazines and make-up best gifts for teenagers Boys buy food and drink, computer games best gift deals best bargains in trainers shop sales DVDs and CDs, girls and boys spend a lot of money on credit for mobile phones best sales deals best bargains in shop sales buses and trains to transport them going out best gifts for teenagers best bargains in shoes shop sales Girls spend a lot of money on clothes best gift deals color colour preferences in clothes, cool sunglasses best sales deals boys buy expensive thins like best gifts for teenagers designer sports clothes and trainers, teenagers save for holidays, best sales deals clothes, mobile phones, birthday presents and electronic goods, teenage accessories, Favourite style of jeans. best gifts for teenagers A typical girl’s shopping list includes mobile phone credit deals best shoes gift deals fashionable quality cool airpods, air pods, fashionable clothes best sales deals the most popular favourite sneakers best gifts for teenagers fancy shoes, sweets, chocolates, magazines, best trainers gift deals best bargains in shop sales lip moisturizer best bargains in  shop sale slots on make-up, well being, teenage decor decorating their room best sales deals teenagers like LED string lantern lights, best gifts for teenagers beauty products for teenagers, denim jackets, scrunchies coolness, fashionable back packs, typical boy’s shopping list includes mobile credit deals, eating out takeaway food and drinks, what teenagers like to buy in clothes best gifts for teenagers computer games, DVDs, CDs, what teenagers talk about best gift deals what teenagers worry about, what teenagers like to do for fun sports best sales deals what cool things do teenagers buy, resale websites like eBay Teenager best high street shop or best online deals currys pc world argos amazon john lewis dell acer samsung raycon bose sony asus huawei HP microsoft in-ear headphones earbuds ipad desktop computer laptop computer for school college university students latest video games consoles apple iphone google high end mobile phones cell phone bargain smartphone xiaomi oppo high tech products latest fashion in trainers latest fashion in shoes latest fashion in mobile phones cell phones

TOP OF PAGE