Offer an explanation for each of the following observations, including the structure of

Chapter 23, Problem 23.62

(choose chapter or problem)

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 12 mole percent tetrabutyl ammonium bromide, (CH3CH2CH2CH2)4N+ Br , is included in the reaction mixture, a product is formed readily. (b) When phenylacetonitrile, PhCH2CN, 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 (p. 1185) 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.