CIE Nov 2015 v3 Paper 4 Q5

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(a) A student carries out some reactions with separate samples of butanal and butanone. 12 PMT butanal butanone The following results are obtained with reagents L, M and N. ( means a reaction takes place.) reagent butanal butanone L M N no reaction no reaction (i) Suggest a possible identity for each reagent L, M and N. LMN[3] (ii) Give the structure of the organic product formed when M reacts with butanal. (iii) What is observed when N reacts with butanone?[1] (iv) What type of reaction is occurring when N reacts with butanone?[1] [1]UCLES 2015 9701/43/O/N/15<br /> PMT (b) The organolithium compound methyl lithium, CH3Li, can act as a source of CH3ions. 13 CH3Li CH3+ Li+ The CH3ion can act as a nucleophile. The reaction between methyl lithium and carbonyl compounds can be used to make alcohols. (i) Suggest a mechanism for the reaction of butanal with CH3 curly arrows, lone pairs and relevant dipoles.ions. Include all necessary CH2CH2CH3 step 1 CH3 intermediate OH H+ CH CH2CH2CH3 CH3 [3] (ii) A chemist decides to prepare the following organic compound G from butanal. H3C OH CH3 CH3 Draw the structure of the organolithium reagent which could be used to prepare G from butanal. [1] [Total: 10]UCLES 2015 9701/43/O/N/15 [Turn over<br />

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