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262_F10_Exam_3_modified

262_F10_Exam_3_modified - 1 The compound below is treated...

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Unformatted text preview: 1. The compound below is treated with NaOD in the presence of a large molar excess of D20 until all exchangable hydrogens have been replaced by deuterium. How many deuterium atoms does the fully- exchanged compound have? 0 & A2 BS C5 D6 CH3 2. How many different enol forms, containing one carbon-carbon double bond, does the compound below possess? Do not consider stereoisomers as separate forms. 0 WH A3 B4 C5 D6 0 3. Which species is not an intermediate in the reaction? 0* 0* 4. Which is the major product of this aldol reaction? Br2 CH3C02H CH2Br + HBr OH 0* O O *& NaOH —> CH3CH20H 5. Which is not the product of an aldol reaction? 0 D 6. Which is the most acidic hydrogen? 0 o “H 22 o \ \fi 0/ H 2 H B /CH2 l_|c 7. Which carbons are potential sites of reaction with nucleophiles? O A iand iii B ii and iii C ii, iii and iv D ii and iv iV iii 8. Select the stronger acid within each pair of ammonium ions. QM QW Q Q iv/NH\ H/ H A iand iii B ii and iii Ciand iv Dii and iv 11. Which is the major product of the reaction? 0 0 II II 1. NaOCZH5, 02H5OH CH3CH20HZCOCH2CH3 + COCH20H3 2. H3O+ (IJH fi 0 0 II II CHTHCOCHzCHa COCCHZCHZCH3 CHZCH3 A B o 0 fi fi CCHZCHZCHZCOCHZCH3 CTHCOCHchs CHZCH3 C D 12. Which is the major product of the reaction? 0 OCHs 1. NaOCH3, CH3OH H3CO —> 2. H3O+ CH3 0 O OCH B 3 CH3 0 o 0 H30 0 H30 0 o OCH3 CH3 A C D 14. Which species does not lie on the mechanistic pathway from reactants to product? o W + NaOCHZCHg —> o CHaCHZOH o o 0 o / O O O A B c 16. Write structures for the carbonyl electrophile and enolate nucleophile that react to give the enone below. I°/ / 17. Write structures for the carbonyl electrophile and enolate nucleophile that react to give the aldol product below. 0 OH 18. The compound shown below is the product of a Claisen condensation. Draw structural formulas for the ester and enolate ion reactants . O O OH 20. Draw the major organic products of the following reactions. 0 + CH3CH2NH2 —> OH + HCI (one equivalent) —> \ N / CH3 N 21. Write mechanisms for the following reactions. 0 o H + H o NaOH 0 2 —> H H C2H5OH H3co OCH3 H300 OCH3 .NaOCH, CH OH OCH3 o 2. 1H30+ + CH3OH ...
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