9701_w15_qp_22
A paper of Chemistry, 9701
Questions:
4
Year:
2015
Paper:
2
Variant:
2

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Halogenoalkanes are useful intermediates in the synthesis of a wide variety of compounds. 2-bromobutane reacts in two different ways with sodium hydroxide depending on the conditions. When warmed with aqueous sodium hydroxide, 2-bromobutane produces an alcohol that exists as a pair of optical isomers. Give the name of the mechanism of the reaction between 2-bromobutane and aqueous sodium hydroxide. Explain why the alcohol produced exists as a pair of optical isomers. Draw the three-dimensional structure of the two optical isomers of the alcohol produced in . Heating 2-bromobutane with ethanolic sodium hydroxide produces a mixture of three alkenes, two of which are a pair of geometrical isomers. Give the name of the mechanism of the reaction between 2-bromobutane and ethanolic sodium hydroxide. Draw and name the structures of the pair of geometrical isomers formed by reaction of 2-bromobutane with ethanolic sodium hydroxide. name name Name the third alkene produced by reaction of 2-bromobutane with ethanolic sodium hydroxide and explain why it does not show geometrical isomerism. Some reactions involving 2-bromopropane are shown. CH3CHBrCH3 2-bromopropane CH3CH2CO2H (and CH3CH(NH2)CH3 which is removed) CH3CH2CH2OH CH3CH(NH2)CH3 X Y reaction 1 reaction 2 reaction 5 reaction 4 reaction 3 hydrolysis reaction 6 HBr State the reagent needed for reaction 1. State the reagent needed for reaction 2. Give the structural formula of X. Name the type of reaction involved in reaction 4 and suggest a suitable reagent. State the name of a solid catalyst for reaction 5. Complete the mechanism for the production of 2-bromopropane from Y in reaction 6 shown below. Include the structure of Y and any necessary lone pairs, curly arrows, charges and partial charges. Y H Br intermediate H3C CH3 C H Br Give the name of the mechanism in . 1-bromopropane is a minor product of reaction 6. Explain why 2-bromopropane is the major product of reaction 6.