SECTION - I SUBJECTIVE QUESTIONS LEVEL - I 1. Acid catalysed dehydration of neopentyl alcohol (CH3)3CCH2OH yields 2 methyl 2 butene as the major product. Outline a mechanism showing all steps in its formation. 2. Identify the final products giving intermediates in each case : (a) F3C – CH = CH2 + HCl (b) O2N – CH = CH2 + HCl 3. An organic compound (D) (C5H8) on hydrogenation gives compound (E) (C5H12). Compound (D) on ozonolysis gives formaldehyde and 2-keto-propanal. Deduce the structure of compound (D). 4. What are the products if addition of D2 to trans-2-pentene in presence of Ni- metal 5. Identify final products of H — C — CH3 H5C2 — C — H D2 ? (a) (I)OsO4, ether (II) Na2SO3 / H2O (b) Now give the product(s) of the following giving mechanism : CH3 | D O / D CH3 C CH CH2 | CH3 2 6. How would you synthesize CH3CH2C CH from CH3CH2I. 7. Propene reacts with HBr to give isopropyl bormide but does not give n-propyl bromide. 8. How can you diffrencitate but-1-ene and But-2-ene? 9. Indicate allylic, vinyl, 1°, 2°, 3° hydrogens in the following compound. Give the sequence of reactivity for free radical substitution. CH3 CH CH CH2 CH2 CH CH3 CH3 10. Explain why the addition of HI to 3,3-dimethylbut-1-ene gives 2-iodo-2, 3-dimethylbutane as the major product and not the 1-iodo-3, 3-dimethyl-butane. 1. (a) An unknown alkene with the formula C7H12 undergoes oxidation by hot basic KMnO4 to yield after acidification only one product. C H (i) hot alk. KMnO4 H C COOH. Identify the alkene. 7 12 (ii) H3O 3 O (b) Starting with compounds C2H2 & C2H5Br outline a synthesis of meso 3, 4 dibromohexane. (c) How would you distinguish between but-1-yne and but-2-yne. 2. One mole of a hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound C5H10Br2. Substance (A) on treatment with cold, dilute alkaline potassium permanganate solution forms a compound C5H12O2. On ozonolysis, (A) gives equimolar quantities of propanone and ethanal. Deduce the structural formula of (A). 3. Compound (A) (C5H8O2) liberated carbon dioxide on reacting with sodium bicarbonate. It exists in two forms neither of which is optically active. It yields compound (B) (C5H10O2) on hydrogenation. Compound (B) can be separated into enantiomorphs. Write the structure formulae for (A) and (B) giving reasons. 4. A compound (A) with molecular formula C5H10 reacts with dilute alkaline potassium permanganate to form compund (B) (C5H12O2). (A) on reduction yields 2-methylbutane and on ozonolysis forms acetone and acetaldehyde. Deduce the structural formula of (A) and (B). Write equation for the above reactions. 5. 448 ml of a hydrocarbon (A) having C, 87.80%; H, 12.19% has a mass of 1.64 g at STP. On hydrogenation it gives 2-methyl pentane. Treatment of (A) with acidic HgSO4 gives a new compound (B) (C6H12O). Compound (A) does not react with ammonical AgNO3. Find out the structure of (A)
SECTION - I SUBJECTIVE QUESTIONS LEVEL - I 1. Acid catalysed dehydration of neopentyl alcohol (CH3)3CCH2OH yields 2 methyl 2 butene as the major product. Outline a mechanism showing all steps in its formation. 2. Identify the final products giving intermediates in each case : (a) F3C – CH = CH2 + HCl (b) O2N – CH = CH2 + HCl 3. An organic compound (D) (C5H8) on hydrogenation gives compound (E) (C5H12). Compound (D) on ozonolysis gives formaldehyde and 2-keto-propanal. Deduce the structure of compound (D). 4. What are the products if addition of D2 to trans-2-pentene in presence of Ni- metal 5. Identify final products of H — C — CH3 H5C2 — C — H D2 ? (a) (I)OsO4, ether (II) Na2SO3 / H2O (b) Now give the product(s) of the following giving mechanism : CH3 | D O / D CH3 C CH CH2 | CH3 2 6. How would you synthesize CH3CH2C CH from CH3CH2I. 7. Propene reacts with HBr to give isopropyl bormide but does not give n-propyl bromide. 8. How can you diffrencitate but-1-ene and But-2-ene? 9. Indicate allylic, vinyl, 1°, 2°, 3° hydrogens in the following compound. Give the sequence of reactivity for free radical substitution. CH3 CH CH CH2 CH2 CH CH3 CH3 10. Explain why the addition of HI to 3,3-dimethylbut-1-ene gives 2-iodo-2, 3-dimethylbutane as the major product and not the 1-iodo-3, 3-dimethyl-butane. 1. (a) An unknown alkene with the formula C7H12 undergoes oxidation by hot basic KMnO4 to yield after acidification only one product. C H (i) hot alk. KMnO4 H C COOH. Identify the alkene. 7 12 (ii) H3O 3 O (b) Starting with compounds C2H2 & C2H5Br outline a synthesis of meso 3, 4 dibromohexane. (c) How would you distinguish between but-1-yne and but-2-yne. 2. One mole of a hydrocarbon (A) reacts with one mole of bromine giving a dibromo compound C5H10Br2. Substance (A) on treatment with cold, dilute alkaline potassium permanganate solution forms a compound C5H12O2. On ozonolysis, (A) gives equimolar quantities of propanone and ethanal. Deduce the structural formula of (A). 3. Compound (A) (C5H8O2) liberated carbon dioxide on reacting with sodium bicarbonate. It exists in two forms neither of which is optically active. It yields compound (B) (C5H10O2) on hydrogenation. Compound (B) can be separated into enantiomorphs. Write the structure formulae for (A) and (B) giving reasons. 4. A compound (A) with molecular formula C5H10 reacts with dilute alkaline potassium permanganate to form compund (B) (C5H12O2). (A) on reduction yields 2-methylbutane and on ozonolysis forms acetone and acetaldehyde. Deduce the structural formula of (A) and (B). Write equation for the above reactions. 5. 448 ml of a hydrocarbon (A) having C, 87.80%; H, 12.19% has a mass of 1.64 g at STP. On hydrogenation it gives 2-methyl pentane. Treatment of (A) with acidic HgSO4 gives a new compound (B) (C6H12O). Compound (A) does not react with ammonical AgNO3. Find out the structure of (A)