chm 2120 answers 1

chm 2120 answers 1 - ANSWERS ASSIGNMENT 1(2009 T.Durst 1(i...

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ANSWERS. ASSIGNMENT 1 (2009) T.Durst 1. + H-Cl H 3 C H 2 C O H .. H 3 C H 2 C O H H (+) + Cl (-) (i) (ii) O H + Na (+) HO (-) O (-) Na (+) + H 2 [irreversible] O + Na (+) H (-) H O (-) Na (+) H 2 O + [reversible] (iii) neither side is strongly favoured since the acid on the left and that on the right are essentially the same strength. If anything. slightly to the right slightly towards the left since water is a stronger acid than is propanol Na (+) (-) NH 2 + CH 3 -CH 2 -O-H NH 3 + CH 3 CH 2 O (-) Na (+) essentially irreversible since sodium amide is a very much stronger base than sodium ethoxide. OR: NH3, pKa 33, is a much weaker acid than ethanol, pKa=16. iv) H 3 C O + O S O O O H H HO .. H 3 C O HO .. .. H (+) + HSO 3 ( -) Hard to say; both sulfuric acid and the 'protonated acetic acid are very strong acids. v) 2. a) 2-methyl-1-hexene; b) 1-bromocyclohexene; c) 1,5-hexadiene; d) trans-1,2- dimethylcyclobutene; e)2-ethyl-1-pentene; f) Z-3-bromo-2-hexene; g) E- 4-hexen-1-ol; h) Z- 2,5-dimethyl-2-hexene; I) trans 2-chloro-cyclopent-3-ene. 3. CH 3 S-Cl a) b) CH 3 -MgBr c) O d) N CH 3 e) HO-Cl f) I-Cl + - + - - + + + + - - - - 4. a) Right, the acetylene is a much stronger acid [pKa=25 ] than ammonia {Ka= 33} b) Right, the secondary carbocation is much more stable than a primary one.
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c) Right, a tertiary carbocation is more stable than a secondary one. d) Left. The tertiary radical is more stable than the secondary radical.
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This note was uploaded on 01/10/2012 for the course CHM CHM 2120 taught by Professor Alysonflynn during the Spring '11 term at Carleton CA.

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chm 2120 answers 1 - ANSWERS ASSIGNMENT 1(2009 T.Durst 1(i...

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