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ABC CLASSES FOR IIT-JEE

ALDEHYDES AND KETONES
D.P.P. - 5

1. An organic comp. (A) of m.f. C5H6 reacted with ethyl magnesium iodide to give (B). (B) reacted
with CO2 to give a salt with on hydrolysis gives (C). (C), subsequently treated with CO2 to give a
salt which on hydrolysis gives (C). (C) subsequently treated with PCl5 and then with Pd/ BaSO4
gives (D). (B) reacted with HCHO and aon further acidification gives (E). (E) when oxidized with
PCC gives (D). A basic solution of (A) showed aromatic characters. Find (A) to (E).
2. An acidic compound A, C4H8O3 loses its optical activity on strong heating yielding B. C4H6O2
which reacts readily with KMnO4. (B) forms a derivative C with SOCl2, which on reaction with
(CH3)2NH gives D. The compound A on oxidation with dil chromic acid gives an unstable
compound . Which decarboxylates readily to E, C3H6O. Give structures of A to E.
3. Predict the product.

4. Identify the missing products in the following sequence of reactions.

5. A compound (A) C5H10O does not react with cold, aqueous KMnO4 and does not add bromine.
When (A) is reduced, (B) C5H12O is formed. Treatment of (B) with hot 20% sulphuric acid yields (C)
C5H10. Comp. (C) instantly adds bromine and decolourise aqueous KMnO4. When (C) is dissolved
in cold 70% H2SO4 and the resulting solution diluted with water compound (D), C5H12O is formed.
Although (B) can be reoxidised to (A), a similar oxidation of (D) of a five carbon atom compound
cannot be accomplish. Assign structures of (A), (B), (C) and (D).
6. A compound (A) (C11H22) when ozonised yields B(C6H12O) and (C) (C5H10O). Mild oxidation of (C)
yields (D) C5H10O2. Compound (B) reacts with NaOCl to yield HCl3 and sodium salt of (D).
Reduction of (B) with LiAlH4 (E) (C6H14O). Dehydration of (E) gives (F) (C6H12). Ozonolysis of (F)
yields (G) (C2H4O) and (H) (C4H8O). comp. (H) does not react with Tollen’s reagent or Fehling’s
solution but does form an oxime and semicarbazone. Write these reactions using structural
formula through out and identify (A) to (H).
7. Complete the following reactions

8. Identify the products. C6H5CHO + CH3COOC2H5

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9. Find product of following sequence is;

10. Identify all the missing compounds.

ABC CLASSES 126,2nd Floor , Kingsway Camp , Delhi-11009,Ph:011-

47041845, www.abcclasses.in