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Ch.21 Prozac (Fluoxetine), the antidepressant is made from compound A. Show how you can make Prozac from starting materials. If Prozac is chiral, how many possible stereoisomers will it form? o, is " . to ou L Cow 0. . Me - H Ne K,C Find a structural formula for C3H6O compound using H-NMR spectrum below. 111) IH III 2 10 an to 9 2 . $ 4 3 2 1 * at (8) Morphine, active molecule in opium poppy 15 one of the most effective painkollters known Disadvantages to use this drug are, it is highly addictive and large doses depresses respiratory - body leading to death (sough-suppressing) has morphine skeleton without disadvantages. Show how you can make this compound frem starting materials of 004 Math Marghter - - - 3th - - (*) * 58-58-56- - - MO - - Ch.14 Draw structure that asatches mass spectrum below. 100 * 80 00 - 201 e 30 29 30 - 50 de 70 80 - 100 110 129 130 TA 150 160 m/5 Viagra (Siddefanil), is * posent inhibition Show how you con syuttesis this foom starting matersals ? - - - N N - mur Ch 15 Write the products of the following sequesces L a 2 NOOH . aur Za(Ca) OH An Am LHBe, perosides 2.211 2.Mg.esber - 9 3. Col * 4. Be An alkane Am Deaw hemiscetal and apcial formed in acid catalyst condition o OH o 1 (a) * EOR (b) o (e) H . MeOH on Ch 17 Complete the following acid-base reactions (a) CH,COOH . - (b) - NaHCO, - COOH QH (c) Nahico, (d) - Ch. 18 A compound C7H1402 has H-NMR. IR spectra shown below. Find a structural formula to a - - 11 - / 2 - - - - M - - - - * Draw . structural formula for each crossed aldol reaction o 9 1 i (a) H + (b) CCH, . CH o 1 (c) . HCH (d) PhCHO CHO Ch 20 Predict the product using Diels-Alder reaction o OCCH, 9 o (a) , (b) . o - H CH, OCOH, o C(CH), 9 COOCH, (e) - NOH, (d) - o COOCH, N= H (e) , - " 2 What - the splitting of the sigral in the ³H b. 2 NMR for the exethyl pessoes of e 3 propane? d. 4 - singles 4 Which compoand gives the following HNMR 6M i * * 5 - b 2 c 3 d. . 5 What ane products of the collision between 6 How many carbon are) presett to . high esergy electross and mothane? molocale which gives an I peak that is * CH, 11.48% of the intersity of the molocular - CH/CH . 5 * b 6 d CH, e 11 4 12 7. What - the maper organic product obtained from the following soguence of reactions? . b. e Mo Hjo d or 0.0 * What is the major organic product obtained from the following reaction? OH OH 1 2 Mgür QM , 4 A - b 2 c 3 d 4 9. What is the major organcic product obtained from the following reaction? : 0104 own 1 2 , . a 1 b 2 c. 3 d. 4 10. Which combination(s) of alkyl bromide and epoxide can be used to peepare the following product by addition of the Grignard reagent derived from the alkyl beomide to the epoxide? OH capher CH§B Br B 1 2 a * only 1 b. only 2 c. only - and 3 d. oely 2 and 4 11. Which conbination(s) of alkal boomide and carbonyl compound can be used so prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the cerbony compound? CHOCES CHYCHIEF CHOCHCHICH . 2 3 4 A only - and 2 b. only 2 and 4 c celly 2 and 3 4. only 1. 2 and 3 12 Whid - the major organic grodact obtained from the following reaction? pos, 2 CHLCH H/QQ 004 1 , , 4 * - b 2 e 3 d 4 13. What - the majoe organic product obtained from the following seguence of reactions? 1 1930 - H QH 194 2 , : I b 2 c 3 d. 4 14 What type of reaction takes place apen 16. Wast - the IUPAC name of the following of a ketome with HCN to compound" cyanobydriat * macleophilic addition o b addition c. mackeophilic substitution CH 4 electroghilic substitution 15 What is the of the oxygon atom of A * * acid b b acid c. N° . 4 v 4 17. Which of the following is not one of Hückel's 6.6 criteria for aromaticity? c 9 . The compound mist be cyclic d. 12 b. The compound must have one p-orhital - each asom of a ring 19. What is the IUPAC name of the following c The compound must be planser or nearly compound? planar so that there is a overlap of p erbitals d. The compound must have a closed loop of als pi electrons NHCH, 18. How many different and a 6)-N-methy including constitutional b. (2)-N-methyl 3-methyl-3-penteramite isomers and stereoisomers, are foemed upoe e treatment of * mixture of butanal and acetione with base? d. (2)-1-methylamino-3-methyl-3-penten a 4 20. Which of the following is the correct order of decreasing acid: strength of the following compounds (mo acidie) less acidie)? D N. NH, OH 1 2 3 * 1>2>3 b 1>3>1 c. 4 3>2>1 21 What is the major organic product obtained from the following reaction? QH 1. CH HJC, CM, Ph OCH/CH, 2 "HyO* PM Sh Ph CH Ph° OCHSONS 1 2 1 4 a I b. 2 c 3 4 4 22. What is the major. product obtained from the following reartion? - 2 no OR NH42 NH , 2 1 4 - 1 b. 2 c. 3 d. 4 23. What is the organic product obtained from the following reaction? 1 Ph I m 1 2 2 9 P Ph 3 4 - b 2 ca d 4 24 Which combination of bromido(s) and dicarbonyli- compound can be seed to) prepare the following product (in * DO on ex CO CHA ascher , 2 OH ce OR 04,048 choppy . - b : 3 d 25 Which of the following of P orbitals of 1,3-busadione has the greatent number of sodes? 1000 2 , 2 8 8 8 2 3 4 b 5 3 d 4 26 What is the reactive intermediate in the 27. What is abéreviated as cin altraviolet- reattion of 1,3-buladiene with HBr in visible . absorhance A esclic bromoniam cation b absorptivity b. allylic cation 0 internity of e allylic radical d of absortiance a 28 What - the trage prodact from the fullowing Hasew or , * - b. : c 3 d. 4 29 What are the relative gesitions of the 6 mase substitaces in the following . orthe 4 para COOM 30. Which of the following undegees the mont rapid acylation upen with chlende and 4 b. c Off d a 31 Which of the following compounts utdergoes the most maped with o en dos, NOW CH . 2 - 4 a - 6 : e 3 d. 4 32. Which accounts for the reaction of 33 Which of the dillowing is ase about 1 with sodiats complesal hydrecide to form They ase resonance- stabilized anices a auchoophilic subolitution (Su2) They ase formed spon additions of . b. Nuckoophile substitution by aucloophile - any halides e They are c Nucloophalic aromatic by d. They - - substitution which take 4 subetnution place by - mocharism 34. Which of the following compounds are tertiary (39) amines? 1. 2. 3. 4. a and 2 b - e 4 1.2,3 and 4 35 What 15 - - the Cope elimination in which - - treated with hydrogen by keat a aydroside sall b - amine e a3" carbocalise d. - amide Manson

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