13. ORGANIC CHEMISTRY. PREVIOUS EAMCET BITS 1. Identify the alkyne in the following sequence of reactions ( 2009 E ) Ozonolysis wacker = CH C CH
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1 1. ORGNI EMISTRY PREVIOUS EMET BITS 1. Identify the alkyne in the following sequence of reactions ( 009 E ) Ozonolysis wacker lkyne B = lindlar 's catalyst = only process + = Pd / BaSO 4 Lindlar 's catalysis () Ozonolysis = (B) ul + (B) O = + Pdl + O O + Pd + l Wacker s process. One mole of alkene X on ozonolysis gave one mole of acetaldehyde and one mole of acetone. The IUP name of X is ( 009 E ) -methyl-- butene -methyl-l-butene butene 1-butene Ozonolysis = = O+ O -methyl--butene (x). Which one of the following statements is true for the optical rotation exhibited by (R, R) and (S, S) - dibromobutene ( 009 M ) The direction and magnitude are same The direction is opposite but magnitude is same The direction is same but magnitude different Both the direction and magnitude are different ns: (R, R) and (S, S) forms are enantiomers of each other. They have equal and opposite optical reactions. 4. Which of the following do not obey uckel s rule for romaticity ( 009 M ) I) II) III) IV) all the above I, II III, IV I, IV ns: Structure I and II obey uckels rule III and IV do not obey. 5. Match the following List I List II ) 4 N I) N, l O, 1000 B) O II) 450 c, heating ) 4 O III) 40% SO 4, 1% gso 4, 60 ( 009 M ) 1
2 D) 6 4 IV) con. SO 4, O, 80 V) Na, dry ether The correct match is B D B D I III IV II I II IV III I IV III II V I IV II Organic hemistry N N + l O ) I 1%gSO4 + O 0% O SO4 B) B III SO 4 = + O 75 80%c O () IV ) = + D) D II 6. The correct IUP name of hydrocarbon X ( 009 M ) -methyl--ethyl pentane -ethyl--methyl pentane -isopropyl pentane 1,1-diethyl--methyl propane -methyl -ethyl pentane 7. The latest IUP name f the following compound ( 009 M) N -ethyl-4-bromoaniline 4-bromo--ethyl aniline 4-bromo--ethyl benzene amine -ethyl-4-bromo-benzene amine ns: Br The latest IUP name is 4-bromo--ethyl benzene amine 5
3 Organic hemistry 8. Which of the following compound (S) has Z configuration ( 008 E ) I) l Br II) l F III) Br F Br l I only II only III only I and III only I) II) igher atomic number l Lower atomic number igher atomic number Br l Lower atomic number igher atomic number Br F Lower atomic number igher atomic number Lower atomic number If higher atomic numbers are same side of the double bond the configuration is Z. 9. What are x and y respectively in the following reaction ( 008 E ) y X Z product butyne E product Na/ N liq and Pd/BaSO 4 + Ni/140 and Pd/BaSO 4 + Na/ 140 and Na/N (liq) Pd/BaSO 4 + and Na/N (liq) ns:1 Na/Li Liq N Pd/BaSO 4 Lidnlars Z 10. ccording to ohn Ingold- Prelog sequence rules the correct order of priority for the given groups ( 008 E ) OO > O > O > O OO > O > O > O O > O > O > OO O > OO > 6 O E
4 4 Organic hemistry ccording to ohn Ingold- Prelog notation system the correct order is O > OO > O > O O 11. The IUP name of is ( 008 E ) Ethoxy propane 1,1- diethyl ether -ethoxy isopropane -ethoxy propane IUP name is -ethoxy propane 1. Identify in the following reaction ( 008 E) chromic N B acid O N N chromic + O + O OO N O N acid () + 4 O B OO N OON ON 1. Identify B in the following reaction nhydrous Zn u = + l + B + l [ ] ll 5O l 5 O ns: = nhydrous + l l ll Zn u + [ ] O 6 4 B l 14. IUP names of the compound ( 007 E ) = O is ( 007 E ) 5-methyl hex--en--ol -methyl hex--en--ol -hydroxy-5-methyl--hexene 5-hydroxy--methyl-- hexene = O 5-methyl hex--en--ol 15. n aqueous solution of an organic compound on electrolysis liberates acetylene and O at anode is ( 007 E ) potassium acetate Potassium succinate Potassium citrate Potassium maleate OOK Electrolysis + O + O+ KO + OOK tanode t cathode 16. Lindlars Na / N B R R atalyst and B are geometrical isomers then ( 007 M ) is cis and B is Trans is trans and B is cis
5 and B are cis and Bare trans ns: R Organic hemistry R is B = 17. IUP name of is ( 007 M ) -methyl--ethyl-1-pentene -methyl-4-methyl-4- pentene -ethyl--methyl-1 pentene -methyl--ethyl-1-pentene = -ethyl--methyl-1-pentene 18. Match the following Set I conc.so4 O ) 170 I B) g powder electrolysis ) OONa D) OONa NaO ao Set II Methane Ethylene Benzene cetylene 5) Ethane the correct set is -, B-4, -5, D-1 -, B-4, -5, D- -4, B-, -5, D-1-4, B-, -5, D- conc.so4 O 17 = ) 170 B) I + 6g Electrolysis ) OONa NaO OONa ao 4 D) R Na/N Lindars atalyst R B 4 5 D 1 Trans 5 R R ( 007 M )
6 Organic hemistry 19. 1,-dibromo ethane reacts with alcoholic KO to yield a product X. The hybridisation state of the carbons present in X, respectively are (005 M) sp, sp sp, sp sp, sp sp, sp Br lc.ko lc.ko = cetylene(x) Br Br In acetylene charbon atom undergoes sp hybridisation 0. The compounds formed at anode in the electrolysis of an aqueous solution of potassium acetate are (005 M) 6 ando 4 ando 4and 4 and O Elelctrolysis OOK + O 6 + O+ KO + node athode 1. + l l 4 is an example of... reaction (005 M) ddition ydrogenation Substitution hlorination l + l l Unsaturated compounds generally undergo in addition reactions. The above reaction is addition reaction.. The chemical and the reaction conditions required for the preparation of ethane are (004 E) l, Zn uo, l, Na, O KOO = OOK, electrolysis O Na, NaO, ao, I+ + I Zn u / O 6. alc KO The following reaction is an example of - reaction Br 4 ddition Dehydrobromination Substitution Debromination ns: (004 E) Br lc.ko lc.ko = Br Br cetylene Br Br In the above reaction Br is eliminated ence it is a dehydro-bromination reaction. 4. The metal used for the debromination reaction of 1,-dibromo ethane. (004 E) 6
7 Na Zn Mg Li ns: Organic hemistry + Zn = + ZnBr Br Br lcohol The metal used is Zn 5. What is the molecular formula of the product formed when benzene is reacted with ethyl chloride in presence of anhydrous aluminium chloride? (004 E) l 6 5 l.l + l l (or) Match the following lists. (004 E) List - I List -II a) ethane two sp carbons b) ethylene six sp carbons c) acetylene two sp carbons d) benzene two sp carbons 5) one sp and one sp carbons The correct answer is B D () Ethane sp carbons ( 001 ) (B) Ethylene = sp carbons () cetylene sp carbons. (D) Benzene 6sp carbons 7. The reagent used for converting benzene to ethyl benzene is (004 M) l, anhydrous ll l, aqueous ll O, anhydrous ll lsol, nhydrous + l ll l 8. Which one of the following compounds decolourises cold alkaline potassium permanganate soleuction? (004 M)
8 6 l 4 8 O ns: Unsaturated compounds decolourises cold alkaline potassium permagarate solution 9. Wet ether is not used as a solvent in Wurtz reaction, because the water present in it. (004 M) hydrolyses RX to RO reduces RX to R destroy the Na metal reacts with R-R ns: The water vapour in wet ether destroys metal. So wet ether is not used in Wurth reaction 0 Organic hemistry O What are X and Y in the reaction 4 + SO 4 X Y (004 M) 6, O, S 4 OSOO, 4, O ns: c O = + SO4 OSO O + SO4 (X) (Y) 1. Which one of the following gases is liberated when ethyl alcohol is heated with methyl magnesium iodide 0 80 O 4 + SO 4 X (00 E) methane ethane propane carbondioxide O+ MgI + Mg O I ` 4 The gas liberated is 4. Wurtz reaction of methyl iodide yields an organic compound X, which one of the following reactions also yields X? (00 M) l dry ether + Mg l + ONa ns: Ether I + Na 6 (X) Lil 4 6+ (X) l l l+ Lil 4 g powder l. Which one of the following reagents is used for detection of unsaturation in alkenes (00 M) NaO + ao cold dilute alkaline KMnO4 l / hv KO / 5O ns: old alkaline KMnO 4 is used in the detection of alkene and alkynes 4. Which one of the following compounds is prepared in the laboratory from benzene by a substitution reaction? (00 M) Glyoxal yclohexane cetophenone exa bromo cyclo hexane ns: ll Ol O l cetophenone
9 Organic hemistry 5. O Rearrangement X O, gso In the following reaction, 4/ SO 4,60 what is X?(001M) O O O = O O = O O gso 4 / SO4 60 (X) test is used for detecting unsaturation in hydrocarbons (001M) Silver mirror Lassiagne s arbylamine Baeyer s Baeyer s test is used in the detection of unsaturation. 7. Which one of the following is used in the preparation of styrene? (001E) O PO 4 Benzene is used in the preparation of styrene. 8. Which one of the following compound converts methyl magnesium iodide to methane in one step (00M) O l 4 O MgI + O + Mg O I 4 9. When acetylene gas is passed through solution, a white precipitate is formed. (00M) aqueous gno ammonical cuprous chloride ammonical silver nitrate aqueous potassium permanganate ns: + gno + N O g g + N NO + O 4 4 X Y In the following reaction X and Y are respectively, SO (00M) ion tube/heating Na SO4 Zn and conc. SO 4 red hot iron tube and fuming SO 4 / Pd,BaSO4dil SO4 ns: Red hot General u tube SO heating Zn/l In the following reaction and B respectively are, 6 l B (00M) l /UV light and 6 Pland 4 l and 6 l and l / U.V light Zn / l 6 l 6 B 4. The reacting ion in the nitration of benzene is (00M) NO NO + NO O ns: Nitration of benzene ring is due to attack of NO + ion (nitronium ion) on the benzene ring. 9
10 10 Organic hemistry 4. ombustion In the following reaction X and Y are, 6 + 7O X + Y + heat (00M) 5O,6O 4O,5O 4O,10O 4O,6O ns: 4 ombustion 6 + 7O 4O+ 6O+ heat X Y 44. The reactants and reaction conditions used in the preparation of ethane are (M00 I, Na / 5O electrolysis 5OOK 4,,7 I,,Zn u,o Zn u I + O 6 + I 45. The reagent used for converting acetylene to oxalic acid is (E00 gso 4/ SO4 gso 4 / OO KMnO 4 / KO ro / SO4 ns: O KMnO / O 5 c OO OO 46. The reaction condition used for converting 1,-dibromo ethane to ethylene are (E00 Zn, alcohol, KO, alcohol, KO, water, Nal, alcohol, lcohol + Zn = Br Br 47. Br B In the following reaction, and B respectively are, 5Br (E00 4 and alcoholic KO / l and aqueous Br / O and aq KO / andbr B Br lcoholic = 5Br KO = 48. The chemicals used for preparing acetophenone are (E 00 ) B) O ) Ol D) anhydrous,b, B,,D,,D,B,D ns: nhydrous 66 + Ol ll 65O 49. What is the minimum quantity of methyl iodide required for preparing one mole of ethane by Wurtz reaction (t.wt.of iodine=17) (E00 14 gram 568 gram 6 gram 84 gram I ++ Na + I 6 + NaI
11 11 Organic hemistry mole of I is required to prepare 1 mole of ethane. moles of I = (1+ x 17) = In organic reactions sodium in liquid ammonia is used as (001 E ) Reducing agent ydrolysing agent Oxidising agent precipitating agent In organic reaction sodium in liquid ammonium used as reducing agent 51. Which one of the following compounds is isomer of 1-butanol (001 M) -methyl--butanol -methyl-1-butanol - methyl --butanol -methyl-1-propanol 1-butanol and -methyl -1-propanol are isomers and they have same molecular formula. 5. The structural formula of -methyl--butene is ( 001 E) = = = = = Structure of -methyl--butene is 5. Which one of the following pairs of compounds are functional isomers ( 001 E) O O, O, ( ) O O, O, O l lcohols and Ethers exhibits functional isomerism and functional isomers have same molecular formula. 54. test is used for detecting unsatunation is hydrocarbon ( 001 M) Silver mirror Lassaigne s arbyl amine Baeyer s ns: Baeyeis test is used in the detection of unsaturated compounds unsalturated compounds decolorises the pink colour of Baeyer is reagent O X O 55. gso 4/ SO4 60 c O O. What is X ( 001 ) O = O O tautomericm = O gso O 4/ SO4 60 c Vinyl alcohol( X) cetaldehyde 56. Methyl benzene can be prepared by reacting benzene with bromomethane in the presence of (000) 1. ll. Br/ l4. Ni / 4.dil. SO4 ll + Br Br ( Friedel craft lkylation ) 57. Ethylene reacts with Br in l4 to form x. When x is reacted with alcoholic KO. Y is formed. ere X and Y are (000) Br Br and Br and 4
12 5Br and 66 Br Br l4 lc.ko = + Br ( X) ( Y) Br and 4 Organic hemistry 1
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