Compound A, C10H8O, mp 121-124°C, is insoluble in water and hydrochloric acid but is soluble in 10% sodium hydroxide, concentrated H2SO4, alcohols, and ether. It does not react with 2,4-DNP or Tollens' reagent. The pH is 5.7 and forms a complex with ferric chloride. Compound A forms a precipitate that melts at 157-158°C when treated with α-naphthylisocyanate and forms a different precipitate that melts at 84-85°C when treated with bromine water.
a. Propose the structure of compound A that is consistent with the above reactions and data.
b. Explain the significance of the:
i. solubility test
ii. 2,4-DNP and Tollens' tests
iii. pH
iv. derivative structures
Compound A, C10H8O, mp 121-124°C, is insoluble in water and hydrochloric acid but is soluble in 10% sodium hydroxide, concentrated H2SO4, alcohols, and ether. It does not react with 2,4-DNP or Tollens' reagent. The pH is 5.7 and forms a complex with ferric chloride. Compound A forms a precipitate that melts at 157-158°C when treated with α-naphthylisocyanate and forms a different precipitate that melts at 84-85°C when treated with bromine water.
a. Propose the structure of compound A that is consistent with the above reactions and data.
b. Explain the significance of the:
i. solubility test
ii. 2,4-DNP and Tollens' tests
iii. pH
iv. derivative structures