3 Carboxylic acid derivatives

 

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Oxford Textbook Pages : 422 - 426

CGP Revision Guide Pages : 168 - 169

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Show Specification Ref : 3.3.9.2

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Question 1 / 4

AQA Jan 2013 Paper 4 Q8 do not write outside the box acyl chlorides such as ch cocl are useful compounds in synthesis the acyl chloride ch cocl reacts with benzene a a i write an equation for this reaction and name the organic product identify a catalyst for the reaction write an equation to show how this catalyst reacts with ch cocl to produce a reactive intermediate marks a ii name and outline a mechanism for the reaction of benzene with the reactive intermediate in part a i name of mechanism mechanism question continues on the next page marks turn over wmp jan chem do not write outside the box b nucleophiles such as alcohols can react with ch cocl the ion ch coo can act as a nucleophile in a similar way state the meaning of the term nucleophile draw the structure of the organic product formed by the reaction of ch coo with ch cocl name the functional group produced in this reaction marks end of questions copyright aqa and its licensors all rights reserved wmp jan chem
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Question 2 / 4

AQA Jun 2012 Paper 4 Q4 do not write outside the box a acyl chlorides and acid anhydrides are important compounds in organic synthesis outline a mechanism for the reaction of ch ch cocl with ch oh and name the organic product formed mechanism name of organic product marks b a polyester was produced by reacting a diol with a diacyl chloride the repeating unit of the polymer is shown below o c ch ch c o ch ch ch ch ch b i name the diol used mark b ii draw the displayed formula of the diacyl chloride used mark wmp jun chem do not write outside the box b iii a shirt was made from this polyester a student wearing the shirt accidentally splashed aqueous sodium hydroxide on a sleeve holes later appeared in the sleeve where the sodium hydroxide had been name the type of reaction that occurred between the polyester and the aqueous sodium hydroxide explain why the aqueous sodium hydroxide reacted with the polyester type of reaction explanation marks c i complete the following equation for the preparation of aspirin using ethanoic anhydride by writing the structural formula of the missing product cooh oh h c h c cooh aspirin ch mark c ii suggest a name for the mechanism for the reaction in part c i mark c iii give two industrial advantages other than cost of using ethanoic anhydride rather than ethanoyl chloride in the production of aspirin advantage advantage marks question continues on the next page turn over wmp jun chem do not write outside the box d complete the following equation for the reaction of one molecule of benzene dicarboxylic anhydride phthalic anhydride with one molecule of methanol by drawing the structural formula of the single product ch oh e the indicator phenolphthalein is synthesised by reacting phthalic anhydride with phenol as shown in the following equation mark oh conc h so heat oh c oh h o phenol phenolphthalein e i name the functional group ringed in the structure of phenolphthalein mark e ii deduce the number of peaks in the c n m r spectrum of phenolphthalein mark e iii one of the carbon atoms in the structure of phenolphthalein shown above is labelled with an asterisk use table on the data sheet to suggest a range of values for the peak due to this carbon atom in the c n m r spectrum of phenolphthalein mark wmp jun chem do not write outside the box f phenolphthalein can be used as an indicator in some acid alkali titrations the ph range for phenolphthalein is f i for each acid alkali combination in the table below put a tick in the box if phenolphthalein could be used as an indicator acid alkali tick box sulfuric acid sodium hydroxide hydrochloric acid ammonia ethanoic acid potassium hydroxide nitric acid methylamine f ii in a titration nitric acid is added from a burette to a solution of sodium hydroxide containing a few drops of phenolphthalein indicator give the colour change at the end point mark marks turn over for the next question turn over wmp jun chem
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Question 3 / 4

AQA Jun 2013 Paper 4 Q4 do not write outside the box this question is about acylium ions rco a the acylium ion h c c o is formed in a mass spectrometer by fragmentation of the molecular ion of methyl ethanoate write an equation for this fragmentation include in your answer a displayed formula for the radical formed marks b the acylium ion h c c o can also be formed from ethanoyl chloride the ion reacts with benzene to form c h coch b i write an equation to show the formation of this acylium ion by the reaction of ethanoyl chloride with one other substance marks b ii name and outline a mechanism for the reaction of benzene with this acylium ion name of mechanism mechanism b iii ethanoic anhydride also reacts with benzene to form c h coch write an equation for this reaction marks mark turn over wmp jun chem
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Question 4 / 4

AQA Jun 2015 Paper 4 Q6 do not write outside the box esters are used as raw materials in the production of soaps and biodiesel a a student prepared an ester by two different methods method alcohol acid anhydride method alcohol acyl chloride a i an ester was prepared using method by reacting ch choh with ch co o write an equation for this reaction and give the iupac name of the ester formed marks equation iupac name of the ester a ii the same ester was prepared using method by reacting ch choh with ch cocl outline a mechanism for this reaction marks wmp jun chem do not write outside the box b the ester shown occurs in vegetable oils it can be hydrolysed to make soap and can also be used to produce biodiesel ch oocc h choocc h ch oocc h b i write an equation for the reaction of this ester with sodium hydroxide to form soap marks ch oocc h choocc h ch oocc h b ii give the formula of the biodiesel molecule with the highest mr that can be produced by reaction of this ester with methanol mark turn over for the next question turn over wmp jun chem
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