8BFall08MT1Key

8BFall08MT1Key - ewe \m 1. (15 pts). Fill in the blank with...

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Unformatted text preview: ewe \m 1. (15 pts). Fill in the blank with the appropriate word or phrase, or circle the correct word in bold face. A. The presence of an alcohol (OH). group on a benzene ring during electrophilic aromatic substitution makes the ring @ electron poor and SWeois the rateof reaction and generally gives Of'ilxo Z 2n {6‘ product. ' UCi-Eo 'Ii . a)“ the presence of a nucleophile. ' C. A meta director has a full or partial 2 charge next to a benzene B. A carbonyl can undergo type reactions in ring. . I D. Lindlar’s catalyst and hydrogen give only the CAS 2 g Y V3 alkene product from an alkyne. E. In formaldehyde (CHZO) the carbonyl@form is more stable in the presence of water. ' F. A meta director in electrophilic aromatic substitution has how many possible resonance structures in the intermediate? 3 G. The formation of an acetal ig reversible / irreversible and can occur in the presence c base / either / neither. H.. An alkyne i less acidic than an alkene. I. An alcohol benzene is a higher priority substituant in IUPAC nomenclature. ' O K in; . l . . . J. An aldehyde 1/ sometimes / never on the C-1 carbon of a chain. K. An alcohol on an alkene will convert to a Uri” n1] functional V group. ' L. A charge that is stabilized by (€50an ncé V is generally more stable than Hypercm). Obi-w . 2. Put the following molecules in order 'of fastest to slowest electrophilic aromatic substitution. (7 pts) . . single charge on a single atom. OH H 0??! Br CHZCH3 N02 NHCH3 A B _ C D E F G G A z: B D C l: Fastest Slowest 3. (24 pts). Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. ’ (3342943 0 CH3CH20H (excess) A 2?); A) \/U\ ' H ' 9r 58mg"; H H2304 ‘ f . 7 OCHacfls “N CN ' S V B) . E (:1 xii-em” = FeC|3 - E . ’ a F . __ Br?“ 9“) W ms 153 mi C) * ‘ r trans H2 / H D) : ——*_—+> #\ Z Viide Lindlar‘s Cat. C‘ 5 4. '(15 pts.). Show a detailed reaction mechanism ferthe following reaction V including resonance structures of the intermediates (if required) and the structure of the expected product. ’ © HNO3 > H2304 Q V a // H . 00.0) Ci _. _ a \ -_v _ I H O +i\' e 6.. /Cl:j ea H10 1;. N Q) (D (I) Q) :0, 4 .A’ G) '0) H 9305, +Hsoq (D O) N0 (D Z G) @2995 v e Q 2 May 5. (10 pts) Show how you would carry out the following synthesis. Use the reagents provided in the column to the right (some reagents may be used more than once, others you may not need at all). Include the structure of the intermediate products formed in each step. Br / D NANHZ CD 27 @szfwau c) Bra-mus} be done. a‘PFIr loss a,” iQ' GroLQrCaw/sig Possible Reagents: Lindlar's Catalyst * Pd/C CH3MgBr NaNH2 AICI3 (CH3)3CCHZBr Br2 H30+ HNQ3 (CH3LCHCH2CI . H2 FeBr3 LiAIH4 6. (10 pts). Circle all the AROMATIC compounds below. 7. '(8 pts) Circle the structure in each pair that is more stable. A) \ VS NH2 ' ‘ » if ~ . B? VS H Br W5 W). COOH C) VS OQN H D) /\O . 8. (12 pts.) Provide the systematic (IUPAC) names of each of the following compounds or draw the appropriate structure. OH 3""‘laUrO‘MI '3‘ Mthufl he‘flfl- L) «one, E B) 0' — Swahfl~S'pheny\pen¥-q.en-z-o fflms M 3 f 3 a? C) 2,4,6—tribromotoluene o H “ _ m. mdkfihenzddghyota D) 3 ' mchw‘ henzddekyob. oh 3 ’ mahfl Benzene Cow‘quth CH3 0 E) H CYC‘UL‘ Game Con-Bad 1 6 Br 3 / 3 y/ 7 3 “gm F) C! E ‘3" “ ‘5’ brow - 3—Ch\orod\ec~-\S’Aiefi‘i-‘lv‘fi ‘L’ was ...
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This note was uploaded on 11/13/2010 for the course CHE CHE 8B taught by Professor Lievens during the Spring '10 term at UC Davis.

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8BFall08MT1Key - ewe \m 1. (15 pts). Fill in the blank with...

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