test2key09 - Chem. 345 Hour Examination II Name Wednesday,...

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Unformatted text preview: Chem. 345 Hour Examination II Name Wednesday, December 2nd, 2009 WSU ID # 1) Consider the reaction AH + H20 ‘3 A1” + H30“) For the following named acids: 1) draw the structure of the acid, 2) give the approximate pKa- of the acid in units of 5, and 3) draw the structure of the conjugate base. Draw structures as clearly as you can and include all lone pair electrons and indicate formal charge where appropriate. (24 points total) Propanal Ethyl acetate Acetonitrile p-Methylphenol pKa LO pKa :Lo pKa_;§_ pKa ID V Hac‘ <55 K“ ' xv” H JEN-iii". E1 acid a a» ° N H L“ 01.? Q -= '. :03 a ‘6'9 1) a "c. I“ g a in )h 10:6 ~' 9- / a ‘ U Benzyl ammonium ion Malonic ester Phenyl acetylene Acetone pKa ID (diethylmalonate) pKa a 5 pKa ,1 ta pKa )0 "E 9 K) I I P! ? __ 5 is“; A b 5 k g q, a a: a tEOJ‘é‘ “fl” ,9 )1 . e2 :3 ‘6: a 4T ’ u 6 a revue . Lu w» '3‘ E {r o o’ 0 7. £- /I § 5: O r O 2) Determine the products for each of the reaction steps show below (2 pts each, 8 pts total). par 3) Mg, ether 80012 PhMOH 3 _. . c) neutralize Grignard rxn AICI3 NaBH4 V Pk M co“, —"' —" methanol EAS - acylation OH 3) Complete the following: (Stereochemistry and regiochemistry may be important, 28 point total). _ O 0 o a) NaOEt, EtOH o 0 NaOH(cat) _' )K a —____ 3! f . —... ) A03 b) neutralization .2K/‘uek ) AH EtOH, heat type Claisen condensation _ type a I 4.9 g , O ' \‘ SOC] ‘-" 6 cu HO 2 CL IT 3 b : \_ OH CHgOH, HCI (gas) \ ) —\ CHZCEZ '55 "fl 9) d type type ' SW €$ L91 ' Lita " eu MgBr a) &0 axlx> ' NaCN b) H3O --~ —* "cad I EtOH type 4.0!. 5 u; 9 l ital-M:- type 8 I365 :LLL 9mm B a) NaOEt, EtOH I O a) NaCN. DMSO H o b 3 r - Br b) LiAng, ethe; , ' ~ g. d) )K/R‘ofi ) K I) ©/\ 0) H30+ \__ I c) NaOH (aq); H30+ heat _ "‘~-’ \ type acetoacetic ester 3 nthesis type 8N2; reduction of a nitrile 0 MIL a) CchOCL AICI3 “ CO: ,4 - W N . CO2Et b) NaOH (a ) n I e) + 0 remove water I J) - q. o) neutralization fr 0“ 3 type type EAS: acylatlon; saponificafion D / \6 V5 1/5 4. Consider the base—catalyzed aldol condensation/dehydration reaction with acetophenone and benzaldehyde. First, draw this reaction (5 points). Second, draw the mechanism of this reaction (5 points, 10 points total). '0 ' ’°. ‘7 o a) m» - -—e m \m “ ‘" *4 ‘e 6 a — o :9! - b) t. 2 . ‘i’k’ ‘H ‘0 O r 3 9N“; N“°_,“(“6) -~ ‘ \Cdg AA 1,“ -._‘:./ é—w '- ‘e‘: :1 V 'i’ (0“ 9 ——————-=-9 \" c p“ (-5-! \AV 1 7‘ gov 5) Provide simple example reactions for the following (mechanisms not required, 5 points each, 20 points total): ' 5a) a reaction that involves decarboxylation 3d 5b) a synthesis of a tertiary alcohol 3 c. 5c) an electrophilic aromatic substitution reaction Pad-L 65. 5d) a base-catalyzed hydrolysis reaction 6) Draw a synthesis of l—phenyihexane—1,6—diol starting from benzaldehyde and S—bromo—l—pentanol , (hint: a protecting step may be required, 10 points). Hair 19 ...
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test2key09 - Chem. 345 Hour Examination II Name Wednesday,...

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