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322bsu07_e4_key

322bsu07_e4_key - Chemistry 322bL Name P 0 Basic Organic...

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Unformatted text preview: Chemistry 322bL Name P 0' Basic Organic Chemistry July 30, 2007 EXAMINATION 4 K13 Answer the following questions in the space provided. Please organize your thoughts and attempt to make your answer as legible as possible. If we cannot read your answer, it cannot be given credit. Please remember that C-C-C-C without rhydrogens and “stick” structural representations will be given N0 credit (except for rings only). You may use the backs of pages for scratch paper. 1. (15) 11. (14) 111. (42) IV. (21) v. (12) TOTAL (104) Chemistry 322bL Examination 4 page 2 July 30, 2007 I. (15 pts) Provide names for the following structures, or structures for the following names, as appropriate. Either IUPAC or common names are acceptable. (a) <3. 2 H/C\N/CH3 .. ‘ c ( . CHa (b) CH3 0 I II CH3~CH-CH-CHZCHZCHz-G—NHCHZCH3 (‘0 .0th Wyclohexqummo —S-—- AWL— (c) N-methyl-p—fluoroacetanilide CH N— (5’0 (a) ’2 ‘0”) F (d) Place the appropriate letter in the space provided for a good example from the structure below of each kind of functional group. Several of these can be answered by more than one letter; however, organize your answer so that you use every letter only once. C 0 Primary amine _D— <1 8%) BHN I-lN—/<H Secondary amine i— V Tertiary amine S:— D Pyridine type of nitrogen A Aniline type of nitrogen E Amide nitrogen C Chemistry 322bL Examination 4 page 3 July 30, 2007 II. (14 pts) For each question below, put a mark in the space provided or (circle) the best answer, as appropriate. (a) Which is the most acidic and which is the least acidic molecule below? (Fill M blanks.) OH OH )::NOZ , ;H F. :HBr iH N02 OCH3 OH luv m_os-\- L__eqs‘r (b) The most acidic molecule below is O\ O\\ O\\ O\\ ‘90 Et \jc-OEt \\C—0Et \C-CH3 (A C\Hz C\Hz CH2 CH2 O//C—0Et O/:C-CH3 \CHz-CH3 \CHz-CH {2) <5 ©CNC <5 (d) Which is the most acidic and which is the least acidic molecule below? (Fill r_w_0 blanks.) H3 CH3 H3 CH3 CH3 CH3 CH3 CH3 CH3 NH( (+) NH( +) H‘NH( +) NH (+) NH<+> (14) © 0 <5 (W OCH3 No2 OCH3 LENS mos’r (e) Nucleophilic addition to the acyl carbon occurs most slowly for which of the following? Chemistry 322bL Examination 4 page 4 July 30, 2007 III. (42 pts) Give the main organic product(s) for the following reactions, or provide the needed reagents and conditions for the transformation shown, as appropriate. More than one step may be required for a given compound. Be sure to note stereochemistry and/or regiochemistry wherever % relevant. Mechanisms need not be shown, and you do not need to balance the equation or show each byproducts. (Note that “No Reaction” is a possible answer.) (a) 0N3 (1) 002. 5 atm H E.) H20,120°C /\ CxOH ————-—-—-—-—-—-——’ ' (+) \- (2) H30 (b) c|;ozH [CH2 /Cl-i /cozH 140°C H020 ‘CHz CH (C) 3" CH3 (d) NH2 (1)NaN02 Cf H2804 ¢\ H20, 5°C __ /- F (2) CuCN \- 3. H3 ‘3 (e) CH30 CH2-CN C”)O\ ¢\ ut—dfi—NHL (1) LiAIH4, Et20 l CH3O CH3O (2) ”2° 0430 CH3 Chemistry 322bL Examination 4 3 ac LV page 5 July 30, 2007 F (t) NH2 1) NaNOz, H20 /\\ ‘ OCH CH30 0450 3 00 H3 2) HBF4 3) heat (g) CH3 U 1) excess CH3I N CH3 excess ('3. NaOCH3 CH3CH20-OCH3 —_> CGHGN J 0 % ~ “v workup ( y n [% Q O 96- & ~ cm, @3600 Chemistry 322bL Examination 4 page 6 0 July30,2007 § ’CH’ C, 3 (i) if 0 O /‘L\ <5 + CHa/lLOACHa —’ \___/ (‘4' ’4 0% Mr "7" N”; (k) I * Br * / * NH : / Z_ + NaNH —_> \1’ g 2 liquid NH3 I + V __ 13 * _ C Lflt N, 3 %¢ £qu (1) NaNOz N (Br H2804 H20, 5°C \ C H3P02(2) (m) F jEé 0; IN 02 NaOEt Q EtOH (n) (1) Li N(IPr)2 0 O THF, -78 °c CH30HZCH2-E-OCH3 0430:4104 Cl-OCH‘é <2)©_/C' Lu (l) (3) H20 workup 7 and: Chemistry 322bL Examination 4 page 7 July 30, 2007 IV. (21 pts) Provide reasonable syntheses (i.e., minimum number of steps, good yields, good stereoselectivity, good regiochemistry, etc. .) for the molecules shown below starting with the indicated starting materials and using any other needed reagents. Be as specific as you can regarding reagents and conditions. Show the product formed from each important step of your syntheses. Be sure to indicate if a step results in formation of an ortho-para isomer mixture, but assume that such mixtures are readily separated. (a) malonic ester + organic reactants of _____________ > $3chsz H 7 or fewer carbons 2 (1502H Cu,(co,E/c)z / iegu‘w- \) MaOEt‘. in EfOl-l \ l 2 Pincu- -Cl ) " {new QfCJ-IZ-C-COJ‘l gar,— cu (cog Be); "A _ c‘gH _ ' [5-6014 2 Q U” l) Nam} M 2 Z uncofié 1 “Sal-IA 2) 1450+ (b) 0 COzEt ,9 CHzCHz-COZH C0028 and CH2=CH—C—0Et ————————————— > 6/ a) diethyl . 6 CH 0-) C0” heptanedloate 6 /“ " “ MaOEé, as :30 Oman” DNaDinAO/ A Lglcofie 2> ”:0 0 ll Chemistry 322bL July 30, 2007 (c) COZH Examination 4 C01” Q ------------- > © 2\ OH \ ‘l (”)0 V Mam AM A Cup (4304(—3 5) @304 // | ‘43 \4M05C‘°"‘\ HLSOHUO‘M') a. H? H3 g mi?— 9 N01 6630‘ page 8 Chemistry 322bL Examination 4 page 9 July 30, 2007 VI. (12 pts) (a) Demonstrate your understanding of the type of substitution reaction shown below by completing the resonance representation of the intermediate. Also be sure to show the structure of the product. (Do not elaborate the nitro groups. You may have more partial structures than you need.) 3 The generic designation for this type of reaction (i.e., 8N2, E1, EAS, etc.) is NA“> who built r a i s K 1' Br (Or 004:102 (5" OCH: Bf 00:0 N02 N02 CH30" N02 /‘ N02 NOzC) 02w ,1 (3r OLH @ A N82 / [30263 ’1 (“6% LUNG. N02 N02 (b) In a few words, indicate why the corresponding reaction of bromobenzene with methoxide anion in methanol at reflux does not proceed. ex r ’ 3641 am on ' w m a %m imam) Mica/MW W17, -¥orm. @ ...
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