Offer an explanation for each of the following observations, including the structure of each product and the
Question:
Offer an explanation for each of the following observations, including the structure of each product and the role of the quaternary ammonium salt.
(a) When sodium benzenethiolate, Na+ PhS–, is mixed with 1-bromooctane in water, no reaction takes place. However, when 1–2 mole percent tetrabutyl ammonium bromide, (CH3CH2CH2CH2)4N+ Br–, is included in the reaction mixture, a product is formed readily.
(b) When phenylacetonitrile, Ph—CH2—C ≡ N, is mixed with aqueous sodium hydroxide and 1,4- dibromobutane, a separate organic layer forms and no reaction takes place. However, when the three components were rapidly stirred in dichloromethane solvent with a few mole percent of tetrabutylammonium bromide [structure in part (a)], a compound with the formula C12H13N was formed in high yield.
(c) When morpholine and bromobenzene are allowed to react in toluene solvent in the presence of the catalyst Pd[P(t-Bu)3]2, a reaction takes place when aqueous NaOH is used as the base and 1 mole percent of cetyltrimethylammonium bromide, CH3(CH2)14CH2N(CH3)3 Br¯, is added to the reaction mixture.
Step by Step Answer:
a Sodium benzenethiolate Nat PhS is a salt and thus soluble in water but not an organic solvent 1bro...View the full answer
