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1.2 [B] HYBRIDIZATION IN ORGANIC COMPOUNDS 16. Number of sp sp 2 2 -bonds present in given compound is: (a) 1 (b) 2 (c) 3 (d) 4 17. What is the hybridization of carbon in compound H — C N ? (a) sp 3 (b) sp 2 (c) sp (d) All of these 18. What is the hybridization of C1 ,C2 ,C3 carbon in the following compound? CH3 — CH2 — CH CH — C C —H 1 2 3 (a) sp sp sp 3 3 3 , , (b) sp sp sp 3 2 2 , , (c) sp sp sp 3 2 , , (d) sp, sp ,sp 2 2 19. What is the hybridization of carbon in the following compounds ? CH — F, CH — Cl 3 3 (a) sp sp 2 2 , (b) sp, sp (c) sp sp 3 3 , (d) sp sp 3 2 , 20. In which of the following carbon is sp 2 hybridized state ? (a) CH — Cl 3 (b) (c) H — C (d) CH3 — NH2 21. Which carbon(s) in the following molecule is(are) sp hybridized? CH — C O || 3 — CH — C C—H 1 2 2 3 4 5 (a) carbon 1 (b) carbon 2 (c) carbons 1, 3 (d) carbon 4 (e) carbons 4, 5 22. What is the hybridization of the carbon atoms numbered 1 and 2 respectively in the following structure? (a) sp sp 3 2 , (b) sp sp 2 2 , (c) sp,sp (d) sp sp 2 , 1.2 [C] INTERMOLECULAR FORCES , BOND PARAMETRES AND HEAT OF HYDROGENATION 23. Which of the following has the strongest van der Waals’ interaction between molecules of the same kind? (a) CH — CH CH CH | CH 3 2 3 3 — (b) CH3CH2CH2CH3 Organic Chemistry : Some Basic Principles and Techniques 3 CH== CH—C≡≡CH 1 2 NH2 2 — C — NH O
(c) CH | CH — C — CH | CH 3 3 3 3 (d) CH3CH2CH2CH2CH3 (e) CH — CH — CH | CH 3 3 3 24. Rank the indicated bonds in each compounds in order of increasing bond strength : (a) 1<2<3 (b) 3<1<2 (c) 1<3<2 (d) 2<3<1 25. Consider the bond dissociation energies listed below in kcal/mol. CH3—Br 70 CH3CH2—Br 68 (CH3 )2CH—Br 68 (CH3 )3C—Br 65 These data show that the carbon-bromine bond is weakest when bromine is bound to a ........ (a) methyl carbon (b) primary carbon (c) secondary carbon (d) tertiary carbon 26. Given the bond dissociation energies below (in kcal/mol), estimate the H o for the propagation step (CH ) CH Cl (CH ) CHCl Cl 3 2 2 3 2 CH3CH2CH2—H 98 (CH3 )2CH—H 95 Cl—Cl 58 H—Cl 103 CH3CH2CH2—Cl 81 (CH3 )2CH—Cl 80 (a) –30 kcal/mol (b) +22 kcal/mol (c) – 40 kcal/mol (d) +45 kcal/mol 27. Benzene can be reduced to cyclohexane when it is treated with hydrogen in the presence of a nickel catalyst under conditions of high temperature and pressure. Predict the signs of H and S for this process. (a) H 0, S 0 (b) H 0, S 0 (c) H 0, S 0 (d) H 0, S 0 28. Compare C — O bond lengths in the compounds given below : ; ; (a) (b) (c) (a) a b c (b) b c a (c) b a c (d) a c b 29. Compare bond length in the given compounds: ; H2C CH2 ; H3C — CH3 (a) (b) (c) 4 Elementary Organic Chemistry for Medical OH CHO OH O C C ≡≡ Bond (1) Bond (2) Bond (3)

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