Halogenoalkanes & benzene questions

Assignment: Questions on Topic 10.2 : Functional groups (Halogenoalkanes & benzene)

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State the equation for the reaction of 1-bromopropane with warm dilute sodium hydroxide solution and name the organic product.

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i. Describe the difference between homolytic fission and heterolytic fission.

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ii. State one example of a reaction where chloromethane undergoes homolytic fission and one example of a reaction where chloromethane undergoes heterolytic fission.

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iii. State the equations for the two examples you have given in ii. and describe the necessary conditions for the reactions to occur.

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When aqueous sodium hydroxide reacts with bromoethane the hydroxide ion acts as a nucleophile and the reaction is known as nucleophilic substitution.

i. Explain why hydroxide ions can act as nucleophiles.

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ii. Explain why nucleophiles are attracted to carbon atoms bonded to bromine atoms.

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iii. Explain why ammonia and cyanide ions can also act as good nucleophiles.

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iv. When ammonia acts as a nucleophile it loses one of its hydrogen atoms as a hydrogen ion. Suggest the structure and also the class of product formed when ammonia reacts with bromoethane.

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Cyclohexene, C6H10, consists of a six-membered carbon ring containing one double C=C bond. Cyclohexene undergoes an addition reaction when it decolourises bromine water.

i. Write the equation for the reaction of cyclohexene with bromine and give the systematic (IUPAC) name of the product.

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ii. Benzene, C6H6, does not decolourise bromine water but does react with bromine in the presence of a catalyst to form a substitution product in which one of the hydrogen atoms on the benzene ring is substituted by a bromine atom. Write the equation for this reaction and state the systematic (IUPAC) name of the product.

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iii. Explain why benzene does not readily undergo an addition reaction with bromine.

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