CHEM2211 Exam 3 2006 another

CHEM2211 Exam 3 2006 another - 2 cnnvuSrRY 221l EXAM III...

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2 cnnvuSrRY 221l EXAM III NOVEMBER 01. 2006 t. ,7 Be sure to read eich quesiion carefully. Partial credit will be assigned where appropriate. To receive'full credit you must answer the question completely. Relax and good luck!! 1. (9 total points) I a) Rank the following compounds in the order of increasing acidity (1 : least acidic): *t I f1 b) Clearly mark the most acidic hydrogen in the following mcjlecules: 2. (E total potnts) ' TOTAL Rank each set of substituents using the Cahn-higold-Prelog sequence rules by numbering the highest priority substituent I and proceeding in decreasing priority, numbering the lowi:st priority.substituent 4. Place the number in the blank below the substituent. 7 5IO ,b{ 'lk (bM -: T l.) k o il ll ' (a) -c-H , I. .\. o tl tl (b) -NHCCH3 I 4 r.- t< - d'l-) -: CH. I- I 'l -cH-CHr CH. I Z -) J TI -/2 .J 5 z 2. (8 total points) 4
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,G* c) AO </ N_H \J Na NH2 + HC=C-611. *-*@ *$p- d( Underliie the favored side for each equilibrium. 3. (12 total points) Give the prodircts of the following acid-bas6 reactions. 3 a) /\l N I T "HCl \-NH .rL t -:r.l ii. rfl {1, "" i ili ;,.1 -t' .i --l , JI .ht . -{!, tq : 'if,?]r- lj.J'.r t Y+p { r91 +.!"4 v:. rr-i ''; ''-iA; - l'l ,a) ii, .i4 i'l "tifi 4 "ir ,:'$ i {,4 il.3 ,tr, t':?'F ,. 'Y.'- jj1:r !i.ii ili-'Ir 1:1{ ltl 'i 11.9 b) + @ NH+ , ffi,x o .l n\llv lvt{ JV r.f- l;2 d) i Fcb(L?n,
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4 4. (20 totalpoints) Complete the following reactions by providing the reactant(s), the reagent(s), or the major product(s). Be sure to indicate stereochemistry by using wedged and dashed lines where appropriate. (a) :(( d OH I I OH I I H2 l1 \' (c) )/ tl L CHI clz t' \.i'.,, t t*l l) \/ \t'/ (t HrO a4'.'*^ -^ 'a '!---t "; 1. BH3, THF 2. H2O2,NaOH. H2O l. Hg(OAc)2,H2O' alt 2. NaBHa
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"5 1. OsOa (h) 2. NaHSO3, H2O Hro- $trrt"'O" LC = ccll.cl H2 (i) Lindlars Catalyst ICI f /r\ ,% e\ CH3!H2CH2C-CCH2CH? .i.
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This note was uploaded on 07/18/2011 for the course CHEM 1211 taught by Professor Atwood during the Spring '07 term at UGA.

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CHEM2211 Exam 3 2006 another - 2 cnnvuSrRY 221l EXAM III...

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