Question

Alkoxide ions react with haloalkanes, or alkyl halides, forming an ether. The generic reaction is RO:1 + R'X → ROR' a) Draw or write the structure of an alkoxide ion and a bromoalkane that can be reacted together to synthesize 2-methoxy-2-methylpropane, (CH3)3COCH3. b) Draw or write the structure of the alcohol that can be deprotonated to form your alkoxide from part 'a'. c) What base would you use to deprotonate the alcohol from part 'b' in order to convert the alcohol from part 'b' into the alkoxide nucleophile from part 'a'. d) Ignoring solvation effects, from the list of solvents below select those solvents that could be used in the reaction from part 'c'. • Acetic acid • 2,2,2-trfluoroethanol Ethoxyethane (diethyl ether) • N-Methylmethanamine (Dimethylamine) Phenol Explain why you chose these solvents e) Draw or write the structure of an alkoxide ion and a bromoalkane different than part 'a' that can be reacted together to synthesize 2-methoxy-2-methylpropane, (CH3)3COCH3. f) Compare your answers from parts 'a' versus 'e'. One of these synthetic schemes is superior to the other. Which is the better synthesis? Explain. For the less favorable synthesis, what other products would be formed?

Answer 1

bromo alt ane (CH3)2 -C-0- CH3 (CH3)3-C-Br + CH3-o@ . I falhway 2 - alkonde (a) (CH3)3-c-ot CHg-BY (6) since the attack by o@ of alkaoxide goes wa SM² pathways 30 pallway is more favoured because bromo alkane is 1° so amount of alt steric hinderence is less compared to ① where it is 30. (bye oo . Nat/or . Na metal (CH3)2 - C-O-H 1 watoto buth oude tertiary bulànol Ethoxyethane is the bes best solvent, because nah , HO is highly basic and elhêr has no acidic proton, So Not are slable in Elher d)