Question

12) Cine ole is the chie + component in eucalyptus oil. It has the molecular formula CH10 and contains no doubt or triple bonds. It reacts with HC to give the dichloride below . What is the structure of cineole? 13) APter heating compound with a catalytic amount of putowene sulfonic acid and water in dichlovo me thane (45 ) for a4 hours. compound c was isolated in 74% yield. Give the mechanism for forming products H1 H2O 14 ) Predict the principal organic poduct for each of the Pollowing reactions, Show Stereochemistry Important. NO RXN Lobelea iPpossible A 1) LAHa dettugletten j) CH 3 CCH). CH26TS - b) c) + 2 or Naot,

Answer 1

12) If it is forming dichloride then there must be either diene or ether present in molecule. C10H180: Degree of unsaturation = (2C+2)+N-H-X)/2 = (22-18)/2 = 2 Thus there are 2 sites of unsaturation. And it is most likely to be a compound with two rings accounting for 2 sites of unsaturation. Hence the structure of Cineole is: HzC CH3 1 H₃C CH₃ 2xHCI CI CH3 C Cineole CH,

43) $. нс Нce: Но :0: Но - н-ot) { - - CH₃ CH3 CH2 : : Н он о во: с "сня Нас 7 н.С

14) a ci H2C E2 is more favourved than SN2 because nuclephile is bulky and strong base. T CH2 - CH H 0 - H2CH2C H₃C CH3 SN2 is more CH, favoured as substrate is 1° alkyl halide. :01 H2CO 1) LAH CHE H3 CH3 CH, 2) H30+ YCH H3C D CHş-(CH2)16CH2-OTS + CH3(CH2)2CH, CH-(CH), CH,-S-CH_(CH2),CHş