a) The alkene drawn here undergoes an electrophilic addition reaction with HBr. i) Give the IUPAC name of this molecule. ii) Outline the mechanism of this reaction. Your mechanism should show the formation of BOTH possible products and should also name both products. iii) Explain why the Markovnikov rule does not predict a major product in this case. b) The common name of the molecule drawn below is diisopropyl ether. Its structural formula is (CH3)2CHOH(CH3)2. to It can be synthesized in two steps using the starting materials propan-2-ol, 2-chloropropane and sodium metal. One of these steps is a nucleophilic substitution reaction. i) Using structural formulae, write two balanced chemical equations representing the two steps of this synthesis. No state symbols are required. ii) Outline the mechanism of the nucleophilic substitution step.

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a) The alkene drawn here undergoes an electrophilic addition reaction with HBr.
Ś
i) Give the IUPAC name of this molecule.
ii) Outline the mechanism of this reaction. Your mechanism should show the formation of
BOTH possible products and should also name both products.
iii) Explain why the Markovnikov rule does not predict a major product in this case.
b) The common name of the molecule drawn below is diisopropyl ether. Its structural formula
is (CH3)2CHOH(CH3)2.
tot
It can be synthesized in two steps using the starting materials propan-2-ol, 2-chloropropane
and sodium metal. One of these steps is a nucleophilic substitution reaction.
i) Using structural formulae, write two balanced chemical equations representing the two steps
of this synthesis. No state symbols are required.
ii) Outline the mechanism of the nucleophilic substitution step.
Transcribed Image Text:a) The alkene drawn here undergoes an electrophilic addition reaction with HBr. Ś i) Give the IUPAC name of this molecule. ii) Outline the mechanism of this reaction. Your mechanism should show the formation of BOTH possible products and should also name both products. iii) Explain why the Markovnikov rule does not predict a major product in this case. b) The common name of the molecule drawn below is diisopropyl ether. Its structural formula is (CH3)2CHOH(CH3)2. tot It can be synthesized in two steps using the starting materials propan-2-ol, 2-chloropropane and sodium metal. One of these steps is a nucleophilic substitution reaction. i) Using structural formulae, write two balanced chemical equations representing the two steps of this synthesis. No state symbols are required. ii) Outline the mechanism of the nucleophilic substitution step.
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