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D.P.P. - 4

1. (i) A ketone (A) which undergoes a haloform reaction gives compound (B) on reduction B on
heating with sulphuric acid gives compound C. Which forms mono-ozonide D. The compound d
on hydrolysis in presence of zinc dust gives only acetaldehyde. Identify A, B and C. Write down
the reacn involved.
2. An organic compound (A) having molecular formula C6H10O, on treatment with methyl
magnesium iodide followed by acid treatment for a long time gave (B). (B) on ozonolysis yielded
(C) and (C) on treatment with a dilute basic solution gave 1 – acetyl cydopentere. (B) on reaction
with HCl gave (D). Identify (A) to (D) and show the mechanism involved in conversion of (C) to 1-
acetyl cyclopentene.
3. An aromatic compound (A), C8H4Br reacts with H2C(COOC2H5)2 in the presence of C2H5O-Na+ to
give (B) compound (B) on refluxing with dil H2SO4 give (D). The compound (D) is a dibasic acid
but on heating does not give an anhydride. It forms a mono nitro derivative (E). in which all the
substituents are at equidistant from one another. Give structures of (A) to (E).
4. When t – butanol and n – butanol are separately treated with a few drops of dil. KMnO4 in one case
only the purple colour disappears and a brown ppt is formed. Which of the two alcohols gives
above reaction and what is brown ppt?
5. Treatment of comp. A (C8H10O) with chromic acid/ pyridine gives B (C8H8O) which reacts with
bromine yielding C(C8H6OBr2). (C) generates (D) (C8H8O3) upon treatment with alkali and
subsequent acidification. Oxidation of D with alkaline KMnO4 and subsequent acidification gives
benzoic acid. Treatment of (B) with SeO2 gives E (C8H6O2) which also affords D when treated with
alkali followed by acidification. Identify A, B, C, D and E with proper reasoning.
6. Identify the product

7. (i) Assuming the absence of any steric hindrance list the following alkenes in deoreasing order of
reactivity towards electrophillic addition.
(a) Cl CH2CH = CH2 (b) Me2C = CH2 (c) CH3CH = CH2 (d) H2C = CHCl.
Explain your order.
(ii) Assume that anti elimination is favoured, illustrate the stereo specificity of the E – 2
dehydrohalogenation by predicting the products formed from (a) meso and (b) either of the
enantiomers of 2, 3 – dibromo butane. Use of wedge – saw horse and Newmann projections.
8. Two isomeric substances (X) and (Y) have the molecular formula C3H6O. On mild oxidation (X)
gives a monobaric acid (Z), sadium salt of which on heating with caustic soda produces ethane. On

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similar treatment namely mild oxidation (Y) remains unaffected but readily reacts with I2 and
NaOH solution producing iodoform what are the compounds (X), (Y) and (Z)?
9. Identify A to J in the following:

(a) (b)

10. Identify A to F in the following sequence of reactions.

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