Here, we are going to synthesis butanoic acid from ethanol and learn the reaction between ethanol and butanoic acid.
Question
Derive butanoic acid by starting from Ethanol. You can only use ethanol as an organic compound and following reagents during the conversion.
Other reactants : Na , Concentrated H2SO4 , H+/KMnO4 , Br2 , Pd/BaSO4/Quinolene , dilute NaOH , organic peroxides , HBr , Alcoholic KOH
In this tutorial, we study about
Steps of preparation of butanoic acid from ethanol is explained below.
Ethanol is heated with concentrated sulfuric acid to give ethene. Ethene is an alkene compound.
Ethene reacts with liquid bromide ( Br2 / CCl4 ) and give 1-2-dibromoethane compound which is an alkyl halide.
1-2-dibromoethane is heated with alcoholic KOH to get ethyne.
Less amount of Na is added to ethyne. Sodium salt of alkyne is formed. This can be used to extend carbon chain.
Ethene reacts with HBr and give bromoethane (ethyl bromide), an alkyl halide compound.
Sodium salt of alkyne and bromoethane react to give the compound with extended carbon chain. That is 1-butyne. This is also an alkyne compound with four carbon atoms.
1-butyne reacts with H2 / Lindlar's catalyst to give 1-butene. Lindlar's catalyst is used to stop hydrogenation upto alkanes.
1-butene reacts with HBr in the presence of organic peroxides to give 1-bromobutane.
1-butanol is given by 1-bromobutane with reaction of dilute NaOH.
Butanol is oxidized to butanoic acid by acidic potassium permanganate ( H+ / KMnO4 ).
Ethanol is an alcohol compound. Butanoic acid is a carboxylic acid. Therefore in the presence of concentrated H2SO4, ester product is given. This reaction is a reversible one. Ester product is ethyl butanoate.
Ethanol is an alcohol and butanoic acid is carboxylic acid. Ethanol, butanoic acid reacts when in the presence of sulfuric acid. It gives the ester, ethyl butanoate as the product.
Ethanol + butanoic acid reactions happens in considerable amount if only in the presence of concentrated sulfuric acid. This reaction is a reversible one. Ethanol and butanoic acid reaction form a pleasant smell due to formation of ester.
As primary alcohols are oxidized to carboxylic acids by strong oxidizing agents. So, butanol can be oxidized to a carboxylic acid compound.
Butanol is a primary alcohol and is oxidized to butanoic acid by following reagants. These are very strong oxidizing agents.
No. Ethanol reacts with butanoic acid in the presence of concentrated H2SO4 acid and give ethyl ethanoate as ester and water as products. If an acid reacts with a base, a salt and water are the products. But ester is not a salt. Therefore ethanol + butanoic acid reaction is not a acid - base reaction.
'But' suffix says there are four carbon atoms in the main chain of organic molecule. No substitute groups are in the butanoic acid. So only four crbon atoms in the molecule. So, we can write the molecular formul as, C4H8O2.
CH3CH2CH2COOH
As earlier decribed in this tutorial, other alcohols such as propanol or methanol can be used to prepare butanoic acid.
When Butanoic acid is reduced by LiAlH4, butanol is given as the alcohol.
If we can prepare butanol from butene, we can prepare butanoic acid. So how to prepare butanol from butene?
Then, butanol is oxidized by a strong oxidizing agent to get butanoic acid as the final product.
Butanoic acid is a carboxylic acid. If you want to prepare a carboxylic acid from an alcohol, it should be a primary alcohol. So butanoic acid has four carbon atoms. Then we know we want a primary alcohol which has four carbon atoms. Butanol is the primary alcohol which has four carbon atoms.
By reacting with strong oxidizing agent, butanol is oxidized to butanoic acid.
To butanoic acid react with methanol, we have to add concentrated sulfuric acid and have to supply heat. As the product, methyl butanoate (an ester) is given.
Molecular mass of butanoic acid = 12*4 + 1*8 + 16*2
Molecular mass of butanoic acid = 88 g mol-1
Amount of butanoic acid = 8.55 g / 88 g mol-1
Amount of butanoic acid = 8.55 g / 88 g mol-1
Amount of butanoic acid = 0.1 mol