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CHM 151 (PS 4.5 F07)

CHM 151 (PS 4.5 F07) - the almost complete regioselectivity...

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CHEMISTRY 151 Fall 2007 Extra Problem Set 4.5 for Exam 1 1) Alkene Reactions a) Write the structure of the major organic product for each of the following reactions. b) Indicate which of the mechanisms involves: i) a carbocation intermediate. ii) concerted addition of A-B to the alkene iii) a 3-membered ring intermediate iv) a catalyst v) rearrangements c) For those reactions marked with an asterix be able to explain the regioslectivity of the reactions with a combination of words and structures. H 2 O cat. H 2 SO 4 1. Hg(OAc) 2 , H 2 O (*) 2. NaBH 4 H 2 (g), Pd/C HBr (*) (*)
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CHM 151 (HLS); Problem Set 4.5 2 2) Methyl tert- butyl ether (MTBE) improves the octane rating of gasoline and can therefore be used as a substitute for lead, an environmental toxin. MTBE can be prepared from 2- methylpropene and methanol and a catalytic amount of strong acid such as sulfuric acid. Using logic similar to that used for the hydration of isobutylene, draw a mechanism that accounts for
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Unformatted text preview: the almost complete regioselectivity of the reaction (very little methyl isobutyl ether is formed). H 3 C O C(CH 3 ) 3 methyl tert-butyl ether 3) Predict the major product of the following reaction and show the mechanism of its formation. Comment on the forces favoring the product you decided was major and other potential products. Hint – there are many potential products you might draw. Look beyond just simple H-OH addition across the double bond. 5% H 2 SO 4 OH CHM 151 (HLS); Problem Set 4.5 3 4) Because you have to think about resonance when determining carbocation and conjugate base stability I wanted to give you a little more practice with the basics Which one of the molecules below is stabilized by resonance? H H H O N O N H O H O HO...
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CHM 151 (PS 4.5 F07) - the almost complete regioselectivity...

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