08_ - P1: PBU/OVY P2: PBU/OVY JWDD052-08...

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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-08 JWDD052-Solomons-v3 May 1, 2007 14:6 8 ALKENES AND ALKYNES II: ADDITION REACTIONS SOLUTIONS TO PROBLEMS 8.1 CH 3 CHCH 2 I Br 2-Bromo-1-iodopropane 8.2 CH 3 CH 2 CC H 2 HB r CH 3 + δ + δ CH 3 CH 2 H 3 CH 3 + Br CH 3 CH 2 CCH 3 CH 3 Br + + (a) (b) (c) CH 3 C CH 3 CHCH 3 CH 3 C CH 3 Cl I CHCH 3 CH 3 C CH 3 Cl I CHCH 3 δ + δ IC l + δ + δ HI CH 3 I H 3 C I + CH 3 123
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-08 JWDD052-Solomons-v3 May 1, 2007 14:6 124 ALKENES AND ALKYNES II: ADDITION REACTIONS 8.3 CH 3 CH 3 CH + CH CH 2 H Cl δ + δ CH 3 C CH CH 3 + H CH 3 2 ° Carbocation 1,2-hydride shift CH 3 CH 3 C CH 2 CH 3 + 3 ° Carbocation Cl CH 3 C CH 2 CH 3 Cl CH 3 2-Chloro-2-methylbutane (from rearranged carbocation) 2-Chloro-3-methylbutane (from unrearranged carbocation) Unrearranged 2 ° carbocation CH 3 CH 3 C CH 3 CH H CH 3 Cl Cl (a) + CH 3 C CH H CH 3 Cl + CH CH 2 H Cl δ + δ CH 3 C CH 3 CH + CH 3 CH 3 2 ° Carbocation 1,2-methanide shift CH 3 CH 3 CH 3 C (b) CH 3 CH CH 3 + CH 3 CH 3 C 3-Chloro-2,2-dimethylbutane (from unrearranged carbocation) CH 3 CH 3 CH 3 H 3 C C CH Cl 2-Chloro-2,3-dimethylbutane (from rearranged carbocation) CH 3 C CH 3 CH 3 CH Cl CH 3
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-08 JWDD052-Solomons-v3 May 1, 2007 14:6 ALKENES AND ALKYNES II: ADDITION REACTIONS 125 8.4 CH 2 H 2 SO 4 CH 2 CH 3 CH 2 OSO 3 H + CH 3 CH 2 OH H 2 SO 4 + H 2 O heat 8.5 (a) Use a high concentration of water because we want the carbocation produced to react with water. And use a strong acid whose conjugate base is a very weak nucleophile. (For this reason we would not use HI, HBr, or HCl.) An excellent method, therefore, is to use dilute sulfuric acid. (from dilute H 2 SO 4 ) + HH H O + + + H H O + H + O H 3 O + H + HO H H O (b) Use a low concentration of water (i.e., use concentrated H 2 SO 4 ) and use a higher temperature to encourage elimination. (c) 1-Methylcyclohexanol would be the product because a 3 carbocation would be formed as the intermediate. + H O H CH 3 + + + H CH 3 H H 3 C H + + H H H 3 O + + H 3 C OH O O
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-08 JWDD052-Solomons-v3 May 1, 2007 14:6 126 ALKENES AND ALKYNES II: ADDITION REACTIONS 8.6 CH 2 CH 3 C CH CH 3 CH 3 HH O H + + CH 3 CH 3 C CH CH 3 CH 3 methanide migration CH 3 + CH 3 C CH 3 CH 3 CH CH 3 CH 3 C CH CH 3 + H H CH 3 H 3 O + CH 3 C CH CH 3 HO CH 3 + + H 2 O CH 3 H H O H H O 8.7 The order refects the relative ease with which these alkenes accept a proton and Form a carbocation. (CH 3 ) 2 C CH 2 reacts Faster because it leads to a tertiary cation, (CH 3 ) 2 C CH 2 H 3 O + CH 3 C CH 3 + CH 3 3 ° Carbocation CH 3 CH CH 2 leads to a secondary cation, H 3 O + CH 3 CH 3 CH 2 ° Carbocation CH 2 CH 3 CH + and CH 2 CH 2 reacts most slowly because it leads to a primary carbocation.
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This note was uploaded on 10/20/2011 for the course CHEMISTRY ES110 taught by Professor Te.li during the Spring '11 term at Central Texas College.

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08_ - P1: PBU/OVY P2: PBU/OVY JWDD052-08...

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