1. The molecular formula of an unknown compound A is C7H14. On ozonolysis, A gave two products B and C where both reacted with 2,4-dinitrophenylhydrazine to give solid derivatives. Compound B gave positive results to both Tollens’ and iodoform tests, while C gave negative results to both of the tests. What is the structural formula of A, B and C. Explain your answer.
1. The molecular formula of an unknown compound A is C7H14. On ozonolysis, A gave two
products B and C where both reacted with 2,4-dinitrophenylhydrazine to give solid
derivatives. Compound B gave positive results to both Tollens’ and iodoform tests, while
C gave negative results to both of the tests. What is the structural formula of A, B and C.
Explain your answer.
2. Compound P, C4H9Br reacts with aqueous solution of sodium hydroxide to form compound
Q, C4H10O. Compound Q decolourised acidified solution of potassium permanganate to
yield compound R, C4H8O which give an orange precipitate when react with 2,4-
dinitrophenylhydrazine. Both compounds Q and R formed yellow precipitate with alkaline
iodine solution. Compound P also reacts with magnesium metal to form compound S,
C4H9MgBr. Compound R reacts with compound S, followed by hydrolysis to give
compound T, C8H18O. Compound T gives off white fumes when react with PCl5.
(a) Determine the structural formulae of P, Q, R, S and T. Write all the reaction equations
involved.
(b) State the IUPAC name of compound T.
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