foreign hello Matt here from chemistrystudent.com in this video we're going to look at amides we're going to talk about what amides are their General structure amide formation using acyl chlorides why amites are weaker bases than a means and for hydrolysis of amites quite a busy video amines and the nucleophilic addition elimination mechanism for preparing amides have been covered in separate videos check the links in the description below before we talk in detail about amides there are a few essential ideas you need to be comfortable with amines are a group of organic compounds that derive or come from ammonia NH3 amines can be aliphatic or aromatic in aliphatic a means one or more of the hydrogen atoms in ammonia has been replaced with an alkyl group an alcar group being a straight or branched carbon chain such as me file or e-file in aromatic amines one of the hydrogen atoms in ammonia has been replaced with an aryl group an Aral group is an aromatic ring group such as phenyl effectively a Benzene ring attached to something else a means can be primary secondary or tertiary depending on the number of carbon groups bonded to the nitrogen in them primary amines have one carbon group bonded to the nitrogen secondary amines have two carbon groups bonded to the nitrogen and tertiary amines have three carbon groups bonded to the nitrogen acyl chlorides are derivatives of carboxylic acids and have a functional group that has a carbon atom double bonded to an oxygen atom and single bonded to a chlorine atom they are highly reactive according to the bronsted Larry definition acids are proton donors and bases are proton acceptors the basicity of a base refers to how easily and readily it accepts a proton and remains as a conjugate acid strong bases readily accept protons and weaker bases less readily except protons recap done let's go amides are carboxylic acid derivatives that have a carbon atom in that's double bonded to an oxygen atom and single bonded to a nitrogen atom amides can be primary secondary or tertiary depending on the number of carbon groups or hydrogen atoms bonded to the nitrogen atom in their functional group primary amites have no other carbon groups bonded to the nitrogen and just have an nh2 group secondary amides have one other carbon group bonded to the nitrogen and tertiary amides have two other carbon groups bonded to the nitrogen for example efan amide is a primary amide that has an nh2 group with no other carbon groups bonded to the nitrogen n e file Ethan amide is a secondary amide as it has an efar group bonded to the nitrogen and N di ephel e-fan amide is a tertiary amide as it has two efar groups bonded to the nitrogen the names for amides can look a bit confusing the eve part of the name here tells us that there are two carbons in the main carbon chain of the molecule and the amide part tells us that the functional group is an amide the strange looking n e file and nn-die file part just tells us that ifar groups are bonded to the nitrogen in the Ethan amide primary amides can be formed from the reaction of an acyl chloride with ammonia acyl chlorides are highly reactive and the nitrogen in ammonia is able to act as a nucleophile as a result when reacted together an addition elimination reaction occurs with a primary amide as the product and an ammonium chloride salt for example ammonia reacts with the acyl chloride ethanol chloride to form ethanamide and ammonium chloride secondary amides can be formed from the reaction of an acyl chloride with a primary amine just as for ammonia the nitrogen in the primary amine is able to act as a nucleophile and again will react with an acyl chloride in an addition elimination reaction for example e-file amine a primary amine can react with ethanol chloride to form n e file Ethan amide and the salt e-file ammonium chloride these reactions and their mechanisms have been covered in much more detail in a separate video check the links in the description below as amides have a nitrogen with a lone pair of electrons they are able to act as bases and accept protons h plus ions however they are much weaker bases than ammonia and amines this is because the carbonyl group in the amide that carbon oxygen double bond causes the nitrogen in the amide group to have a lower electron density around it than it would normally have when bonded to carbon the oxygen atom has a high electronegativity and attracts electron density towards itself and away from the carbon atom ending up with a partial negative charge and leaving the carbon atom with a large partial positive charge as a result the nitrogen also a highly electronegative element isn't able to put as much electron density away from the carbon atom towards itself as it normally would this makes the lone pair of electrons on the nitrogen less available and makes it harder for the nitrogen atom to accept and hold on to a h plus ion and as a result this means the amide has a low basicity a weak base and in amine however the carbon atom than nitrogen is bonded to has nothing else pulling electron density away from it meaning that nitrogen is better able to attract electrons towards itself this increases the electron density around the nitrogen atom and increases the availability of its lone pair of electrons making it easier for a h plus ion to bond to it the carbon group in an amine even actually helps push electron density towards the nitrogen in what is called the positive inductive effect and this not only increases the availability of the lone pair of electrons on the nitrogen but also helps stabilize the positive ion formed when the nitrogen accepts a h plus ion meaning the amine is able to hold on to the h plus ion all of this makes amines much stronger bases than a mites the basicity of amines and the positive inductive effect has been outlined in more detail in a video about the basicity of amines check the links in the description below primary amides can be hydrolyzed and turned into a carboxylic acid and ammonia and a secondary or tertiary amide can be hydrolyzed and turned into a carboxylic acid and Amine Alkali or acid hydrolysis breaks the bond between the carbon and nitrogen atoms in the amide group ultimately splitting it apart if an acid is used the process is called acid hydrolysis and a carboxylic acid and ammonium salt is formed if an Alkali is used the process is called Alkali hydrolysis and a carboxylate ion is formed acid must later be added to obtain the carboxylic acid if Alkali hydrolysis is used this is because a carboxylic acid can't form in alkaline conditions it would instantly lose a h plus ion and reactive hydroxide ions four minutes carboxylate ion and water for example if the primary amide e-fan amide is heated with sodium hydroxide it will be split apart into an f and no8 ion and ammonia as the solution is heated the ammonia will leave as a gas and a solution of sodium ethanoate will be left behind to obtain ethanoic acid dilute acid would then have to be added if Ethan amide is heated with dilute acid hydrochloric acid for example then the carboxylic acid ethanoic acid will form and this time the ammonia released will accept h plus ions present in the solution from the acid forming positively charged ammonium ions that will form ammonium salts with the negative ions from the acid molecules for example ammonium chloride if hydrochloric acid is used so to summarize amides are carboxylic acid derivatives that contain a carbon atom that is double bonded to an oxygen atom and single bonded to a nitrogen atom the nitrogen atom can either be bonded to just hydrogen or other carbon atoms depending on whether amide is primary secondary or tertiary primary amides have no other carbon groups bonded to the nitrogen in the amide group secondary amides have one other carbon group bonded to the nitrogen and tertiary amides have two other carbon groups bonded to the nitrogen primary amides can be formed by the reaction of an acyl chloride with ammonia in a nucleophilic addition elimination reaction secondary and tertiary Amite can be formed by the reaction of an acyl chloride with a primary or secondary amine also in nucleophilic addition elimination reactions amides are weaker bases of an amines the oxygen atom in the amide group pulls electron density away from the carbon atom due to Oxygen's high electronegativity this leaves the carbon atom with a partial positive charge reducing the amount of electron density the nitrogen atom can pull towards itself meaning that carbon nitrogen bond isn't as Polar as it would otherwise be as a result the lone pair of electrons on the nitrogen atom is less available making it harder for the nitrogen to accept and hold on to a h plus ion given amides a low basicity in an a mean the positive inductive effect from alkyl groups makes the lone pair of electrons on the nitrogen more available and can help stabilize a positive charge on the nitrogen if it accepts a h plus ion increase in the ability of amines to act its bases and making them stronger bases than amides a mites can be hydrolyzed using a dilute acid or Alkali in acid hydrolysis an amide is heated with a dilute acid and broken apart into a carboxylic acid and an ammonium ion in Alkali hydrolysis an amide is heated with sodium hydroxide solution and broken apart into a carboxylate ion and ammonia or in amine depending on the amide of its hydrolyzed I hope you found this video useful please check out other relevant videos in the links given in the description below and visit chemistrystudent.com for free notes and revision materials