Ff ' 3[ * ,. ,fF O

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' ff '3[ * ,. ,fF oiP)TJ)I#JLJi 1J : ! f§-.Lfl J,i:ijtft* ijJiQ.tiiJi)m1c·*01*4El 1\ . 2801 ti\ *4 El ·1f l1c*2. 1f * -fy * tt AJ4 , ***M · 3. i0IT- -1 - .;;g.J:.tl urrm !:. M1 JI& pq ,Ji tif :f M. '* - # ·4. ;f .Jfl 1-!t* RnaJi 5. .;f .tifffl M:f 1 *A M;f .m ·tt4i m :t : Jfl2B - : *C¼** ) M *m · *-#m tt ·.f. A. tJI-M.N1 .&.illil.AJ.I i!- J 71J lTTJ 1 §.*j;o ,1l.*'tf§,ftVfM,it ti J:. r *IN001-'F i. l 1f6. j Jt 1J 'i!.#t4 ll o1} i(.* tt

FJTJJJ.#JU}IJ : !! l-1-;fl. J{J,t# i JJl. 01 #JI.( ffl;;Jf # §({t, #JI.)1t ) : ;tr {t. (2801)# 6 1l ' i 1 1l1. Which one of following structures has the lowest strain energy?(B)(A)HH ( ' h '-··'(D)(C),,.HHct(H(t)H ,. -(E),,.:.HCDH . ·,,.HH2. Which one of following structures is most stable based on resonance comformation.(A)(C)(B)(D)(E)00 vvvl@JJl@,.tl3. Which one of following structures has the lowest pKa?(A)(B)M)MoHAc, OHOH(D)(C) Cl(E)Cl OH c, 4. Which one of following structures has the lowest strain energy?(A)(B)(C)(D)(E) OH

iPJrJ)IjJl.)i 1] t;t# §(:1-1-1-f.I J{Jl,# ix; Jjl. iJI.( ffl 1b iJi)1\ ) : ;Jf 1!:.*(2801)# 6 Ji: , J 2 Jl5. Which one of following structures has the lowest strain energy?(A)(B)(C)(E)(D)6. How many structures are meso compounds in following figure?(A) 1 (B)2 (C)3 (D)4 (E)5ClNA . ,. C l/V.'Cl7. Which statement is correct for the reaction shown below?1-chloro-2,4-dinitrobenzene NaOH 2,4-dinitrophenol(A) This reaction is an electrophilic aromatic substitution.(B) This reaction is a SN2 substitution.(C) This reaction is a nucleophilic aromatic substation.(D) Substituted benzyne is the reaction intermediate.8. Assuming the ionization energy of a hydrogen atom is E, estimate the 4f orbital energy for a Li2 cation:(A) 3E/4(B)-3E/4(C) 9E/16(D)-9E/ 16(E) E/4

i Flf Jfi jJI.J3 l : .i. -U- .r.fl Jf :!.i#* i iJt J)l1 -t # §(0i #JI.( ffl 1b* #JI.)1\ ): :,r 1b*(2801)# 6 1l 1jt 3 1l9. Please indicate which type of compounds are not derivatives of the nucleophilic acyl substitutionreactions.(A) Ester(B) Amindes(C) Acid anhydrides(D) Amines10. Which of the following compounds is a suitable base to prepare ester enolate of ethyl acetate?(A) Lithium diisopropylamide(B) Pyridine(C) Diisopropyl amine(D) Pyrrolidine11. Which of following addition reactions ofalkenes occur specifically in an anti- fashion:(A) Dihydroxylation using OsO4, H2O2(B) Addition ofBr2(C) Hydroboration-oxidation(D) Hydrogenation using H2-Pt12. The conversion of2-pentanone to butanoic acid is best accomplished with:(A) h, NaOH(B) NaBR4(C) Cr03(D) AgiO13. A molecule has three degrees ofunsaturation. In this molecule there would be(A) three rings(B) three double bonds(C) two rings and one double bond(D) one ring and two double bonds(E) any of the above

?}T JjI fJ1Jj1J : 1. I- .L f [ J,! fr ,1; - J)l fJl( 1' ffl 1t. fJl) t # §(1\ ): 1t. (2801)# 6 1't 4 14. In a solution ofaspartic acid (pKa 7.4) adjusted to a pH of2.74,(A) the ration of asparate to asparatic acid is IO to 1.(B) the ration of asparate to asparatic acid is 100 to 1.(C) the ration of asparate to asparatic acid is 1000 to 1.(D) the ration of asparate to asparatic acid is 1 to 10.(E) the ration of asparate to asparatic acid is 1 to 100.15. Addition ofBr2 to (E)-hex-3-ene produces .(A) A meso dibromide.(B) A mixture of enantiomeric dibromides which is optically active.(C) A mixture of enantiomeric dibromides which is optically inactive.(D) (Z)-3,4-dibromo-3-hexene.(E) (E)-3,4-dibromo-3-hexene.16. The Diels-Alder reaction is a concerted reaction; this means:(A)A mixture of endo and exo products is formed.(B)All bond making and bond breaking occurs simultaneously.(C)The products contain rings.(D)The reaction follows Markovnikov's rule.(E)The reaction is highly endothermic.17. Which of the statements below correctly describes an achiral molecular?(A)The molecule has a non-superimposable mirror image.(B)The molecule exhibits optical activity when it interacts with plane-polarized light.(C)The molecule has an enantiomer(D)The molecule might be meso form18. Which is the reaction major product when benzene reacts with propene in the presence of HF?(A) propylbenzene(B) iso propylbenzene(C) 3- propylbenzene(D)l- propylbenzene

tf'JrJjI jJI.]] 1] t # El:1- 1-.:LfX J,i:!i,# ti JjI 179 iJI.( ffl 1c jJI.)c1 ) : 1c (2so1)# 6 1\ , i s J19. When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is:(A)2-nitropyridine (B) 3- nitropyridine (C) 4- nitropyridine(D)3-aminopyridine (E) 4- aminopyridine20. What is the major product which results when tetrahydrofuran is reacted with excess HBr?(A) 1,2-dibromobutane(B) 1,3-dibromobutane(C) 1,4-dibromobutane(E) 3-bromobutan-1-ol(D) 4-bromobutan-ol21 . Which of the following compound is the least reactive toward 1-propanol in Nucleophilic AcylSubstitution?(A) acetyl bromide(B) acetamide(C) acetic anhydride(D) ethyl acetate22. A molecule has three degrees ofunsaturation. In this molecule there would be(A) three rings(B) three double bonds(C) two rings and one double bond(D) one ring and two double bonds(E) any of the above23. Which of the following amines is most basic?(A) aniline(B) N-ethylaniline(C) N,N-diethylaniline(E) pyrrole24. Which reagent would convert cyclohexene into a cis-glycol?(A) cold dilute potassium permanganate(B) hydrogen peroxide and aqueous acetic acid(C) ozone and moist zinc dust(D) periodic acid(E)sodium tert-butoxide in chloroform(D) piperidine

i ?Jr JJI iJI. %J : 1- -1- 1. fl. :ti it# i iY¾ - :t:Jl1:tt # §(1.iz ) : iJI. (J.tm1t. iJI.)1f #\11:. (2801)# 6 1i J 6 1l25 . What statement does NOT apply to the boiling points of alkanes?(A) The boiling point increases as the length of the carbon chain increase.(B) Straight chain alkanes have a higher boiling point than their branched isomers.(C) The boiling points are influenced by hydrogen bonding.(D) Because they are nonpolar; alkanes have lower boiling points tha other organic compounds ofsimilar molar mass.(E) The boiling points are affected by van der waals attractions

14. In a solution ofaspartic acid (pKa 7.4) adjusted to a pH of2.74, (A) the ration of asparate to asparatic acid is IO to 1. (B) the ration of asparate to asparatic acid is 100 to 1. (C) the ration of asparate to asparatic acid is 1000 to 1. (D) the ration of asparate to asparatic acid is 1 to 10.

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