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A Resonance” Educating for better tomorrow TARGET : JEE (ADVANCED) 2016 Course : VIJETA & VIJAY (ADP & ADR) Date : 13.04.2016 TEST INFORMATION DATE : 17.04.2016 CUMULATIVE TEST-02 (CT -02) Syllabus : Physical : Mole concept, Equivalent Concept, lonic equilibrium, Electrachemistry, Inorganic : Inorganic Nomenelature, Periodic table, Chemical bonding and Coordination compounds, Organic : Organic Nomenclature, lsomerism, Stereoisomerism, GOC, POC, Tautomerism, Acids & Bases. DPP No. # 03 (JEE-ADVANCED) Total Marks : 169 Max. Time : 117 min. Single correct Objective ('-1" negative marking) Q.1 to Q.16 (3 marks, 2 min.) [48,32] One or more correct objective (no negative marking) Q.17 to Q.22 (4 marks, 2 min.) —_—_—[24, 12] Assertion and Reason ('-1' negative marking) Q.23 to Q.25 (3 marks, 3 min.) [09,09] Comprehension ('-1' negative marking) Q.26 to Q.33 (3 marks, 2 min.) Single digit integer type ('-1" negative marking) Q.34 to Q.40 (4 marks, 3 min.) Double digit integer type (no negative marking) Q.41 (4 marks, 3 min.) Match the Following (no negative marking) Q.42 to Q.45 (8 marks, 6 min.) 4. Which of the following compounds might be useful to the chemist trying to increase the optical purity of the (@) sample ? _ Hog OC ® ® CO © Ho bow 2 ‘Sum of total number of chiral centres (x) and total number of pairs of enantiomers (y) for following structure is aK we ©3 wos os 3. Determine the absolute configurations of the chiral centres inthe following compound (Aa=R:b=S (B)a=Rib=R ()a=S;b=8 4. The binaphthol (np) is (A) an optically active compound having chiral centre (B) an optically inactive compound (©) ameso compound (O) an optically active compound without having chiral centre RESenence 10. 1, ‘The element(s) of symmetry present in the following molecule is/are () Alternating axis of symmetry (i) Plane of symmetry (Axis of symmetry (WV) Centre of symmetry (A) Landi ®) Landi (©)1, Mand it O11 Manaiv Which of the following structure has incorrect IUPAC name Me. Me a) 0 2-Bromo-5,5-dimethylcyclopent-3-en-1-one Br No, CHO. ) 6-Methoxy-1-nitrocyclohex-t-ene 2 Of} 6-(Cyclobut-2-enyNhex-2-ene CONH, Br, N=O oO TS 2-Bromo-6-nitrosobenzenecarboxamide How many possible isomeric alkenes give 2,3-Dimethylpentane on catalytic hydrogenation. as (86 ©8 05 Order of enolic content ()P>Q>R>S — (B)P>S>R>Q_— (C)R>S>P>Q_— (DJS >R>P>Q Write the total number of benzenoid structural isomers of molecular formula C,H,O, which can give Fehling test, (A)2 (83 (4 (O)1 Dipole moment of above compound will be A)L4.11D;16.87D — (B)-6.87D; 14.1 (C)-4.11D; 14.110 (D)1-6.870;1-0D Which of the following compound is most stable ? CH, ns Aco’ iS mw SS | Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS Metin 12, 13, 14. 15. 16. ae 18° Which statement about the following equilibrium is true ? pow + 40 ee fon + on (A) The equilibrium favours the products (8) t-Butoxide is the dominant anionic species in the equilibrium (C) Water is the weaker acid than t-butyl alcohol (O) t-Butoxide is stabilized by resonance Which of the following has lowest pk, value? er ® ©Oyer-O) © CONS o OOO The heat of hydrogenation for 3-methylbut-1-ene and 2-pentene are -30 kcal/mol and -28 kcal/mol respectively. The heats of combustion of 2-methylbutane and pentane are -784 kcal/mole and ~782 kcal/mol respectively. All the values are given under standard conditions. Taking into account that combustion of both alkanes give the same products, what is AH (in kcal/mol) for the following reaction under same condtions ? www ees (ayo (8-4 2 2 Meal: : NM sascsrengnor IO) sostimes more tna 4, +-cimetnyaminenephatne. 1.84aimanpanin) ‘apihalene Reason for high basic strength is (A) Resonance (8) Steric inhibition of Resonance (©) Ortho effect ()Hyperconjugation Among the following, the most stable isomeris OH OH OH on ») 2m @ : : OT © Aron OL. © EF Correct statement is/are regarding carboxylic acids having molecular formula (C,H,0.) containing atomatic fing (A) The total number of carboxylic acids (with one benzene ring) is 4 (8) Out the three Toluic acids, the ortho isomer is the strongest acid (C) All these Toluic acids are weaker acids than benzoic acid. (O)Allthese are weaker acids than H,CO, Select the correct statement(s) about the following reaction. traces of or GH ‘ OCH, ‘OCH, oH 6 é 6 (1) (R) Thalidomide derivative a) (A) Itis an isomerisation reaction. (8) Itis a racemisation reaction. (C) The reaction is passing through the process of enolisation. (OD) land are tautomers. mw SS Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS eben 19" 20. ae 22" 23. Which of the following has correct IUPAC name ? mori 4-Chioro-N-(@-clorbuybutanamide ‘4 1 FAL F soy ®) 1,1-Dichloro-4-mercapto-2-methyl-5-trfluoromethylheptane-3-sulphonic acid H i Os 9 © 3-Formy!—-4-methyl-5-oxopentanoic acid OH o —s§ ©) oi Ethylmethylbenzene-1 ,2-dicarboxylate Mark the compound given below which have atleast one meso stereoisomers. (A) Gyclopentane-, 3-dicarbaldehyde (©) Hexane-1,2,3.4,5,6-hexol (€)2,3,4,56-pentahydroxyhexanal (©)2,3-Dinydroxybutanedioic acid Br cH, cH, Br Choose the correct option/s according to the given compound. (A) Total stereoisomers are five. (B)All stereoisomers are optically active (C)Alllstereoisomers are optically inactive. (D) Four stereoisomers have plane of symmetry & one has centre of symmetry Which of the following are (configurational) enantionmers of (P) ? Br H. 1 H cH, cH, cH, Hy ef Hi, o H 4, 1H cl cH, a) 8) © © H er Br Ho BF uJ # Br cH, cH, cH, a Statement-1 : Trinydroxyglutaric acid (HOOC ~ (CHOH), - COOH) exist in four stereoisomeric form, two of ‘which are optically active while other two are meso forms. Statement-2 : It contains two asymmetric and one pseudoasymmetric carbon atoms. (A) Statement-t is true, Statement-2 is true; Statement-2 is correct explanation of Statement-1 (B) Statement-t is true, Statement-2 is true; Statement-2 is NOT correct explanation of Statement-1 (©) Statement-1 is true, Statement-2 is false. (0) Statment -1 is false, Statement.2 is true, mw SS Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS Meiealinaehd 24. 25. Statement-1 : There is evidence for existence of N-methylacetamide in two structural form | and Il as shown below. ch Heme yh HB yc eM of ‘CH, 1 1 Statement-2 : Rotation about C-N bond is restricted due to resonance, (A) Statement-1 is true, Statement-2 is true; Statement-2 is correct explanation of Statement-1 (B) Statement-1 is true, Statement-2 is true; Statement-2 is NOT correct explanation of Statement-1. (C) Statement-1 is true, Statement-2is false. (D) Stalment -1 is false, Statement-2 is true. Mew Ht Hy Me sn he HAN. re moe He HY Me (A) (8) Statement-t : Ais optically active & B is optically inactive. Statement-2 : A has centre of symmetry. (A) Statement-t is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1 (B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1 (C) Statement-1 is True, Statement-2 is False. (0) Statement-1 is False, Statement-2 is True. Comprehension #1 26. 27. 28. ‘The compound shows below in the diagram, on treatment with acid catalyst isomerizes and equilibrium is established among the stereoisomers, CH,-CH-CH-CH, where X +H or CH, a The equilibrium mixture contains all the three stereoisomers of this compound. Specific rotation of pure dextro isomer is +62" while the specific rotation of the equilibrium mixture is + 22°. Also the equilibrium mixture contains 20% of the meso isomers. Answer the following three qeustions based on the above information, ‘The percentage purity of the equilibrium mixture is (A) 28% (B)35% (46% (0) 54% The percentage of racemic mixture present in the equilibrium mixture is (A) 35% (B)45% (65% (0) 80% Composition of equilibrium mixture is (A) 20% meso, 58% dextro and 22% laevo (B) 20% meso, 60% dextro and 20% laevo (C) 20% meso, 54% dextro and 26% laevo () 20% meso, 30% dextro and 50% laevo Comprehension #2 A research scholar synthesised the compound A in the laboratory cH, Ais® Qcn, ‘CH.-COOH He wanted to study this compound in acidic medium and kept for some time with heating. After an hour, ‘when isolated the compound, to this surprise, he got the mixture of two compounds B, C. He studied their properties and compound them with A a B c Reaction with NSHCO, TCO; Noreaciion No reaction Blue litmus red No No NaOl No No Yellow ppt FAGINH.),I* No No Silver minor THint: A —"°"", B+ cy mw SS Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS eceanee 29. 30. at Compound Bis fe} Oo a tk ® Chon © Q (O)None ‘OH “ ‘CH,-OH Compound Cis Monch, ICH CHACHO HEH @)cH-cH-0 Bis formed due to (A) Cleavage of C-O bond followed by esterification between -COOH & —OH present. @ Decarboxylation of COOH group (C) Oxidation of -CH,COOH into-COOH (0) None: Comprehension #3 32. 33, 34. 36. 36. Tartaric acid [HO,CCH(OH)CH(OH)CO,H] was an important compound in history of stereochemistry. Two naturally occuring forms of tartaric acid are optically inactive. One optically inactive form (P) has a melting point of 210-212°C and can be separated into two optically acitve forms, whereas other optically inactive form (Q) cannot be resolved further. Optically inactive form Qis COOH cooH 7 Hog EM c © I (0) none of these c. no7 Au CooH A optically inactive form Pis (A) Optically inactive due to internal compensation. (8) Optically inactive due to presence of plane of symmetry. (©) Optically inactive due to external compensation (©) Optically inactive due to intramoleuclar hydrogen bonding Allegra, a common prescription drug with the structure shown below, is given for the treatment of seasonal allergies, How many stereogenic carbon does Allegra possess ? if Je Ms (1) NaOCl, . ‘OH Sy Xo) He @) The total number of isomeric products formed is ‘What is the number of all the structural isomers of octane with five carbons in their principal chain ? mw SS Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS PAGE NO. 37. 38. 39. 40. a. 42. 43. How many optically active compounds are possible in the following reaction ? t Q rowehinan Product (S) ba CH, 22 , + Hooc-d coon & (mole) (2 mole) (1 mole) How many bonds are presentin compoud A ? Assmallest, optically active, acyclic alkane can obtained by catalytic hydrogenation of any of the five structural isomers of an alkene. How many of these alkenes are chiral ?| Calculate sum of X and Y in the given molecules, X=Number of molecule having plane of symmetry Y = Number of molecule having centre of symmetry HOH Br 0 @ Ope» 8r “ot é Ho CH, A 2M solution of glyceraldehyde (HOCH. ~CHOH-CHO) was placed in a polarimetertube of length 100 mm. Using the sodium D line, a rotation of 7.2° was found in clockwise direction at constant temperature. Determine the specific rotation of the compound. Match the column Column (Molecule) Columns Property) oH, cI “ — (©) Chiral atom is present ef 1 6. ox> (@ Molecules chiral 0 om, © > cH, ( Plane of symmetry is present © cma (8) Centre of symmetry is present Match the column Column (Compound) Column-lI (used for separated between) (A) NaHCO, solution (P) CHy-CH,-NH, & CHy-CH,-NH-CH, () Naso, (@) Ph-CO-NH, & Ph-CH,-NH, (©) dil. HCI (0 CHy-CH,-OH & CH,-CH=0 g o KOH Ph-COOH & Ph-OH c yon {O)-p © mw SS Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS PAGE NO. Match the column (1) and (I). Column - (I) (Molecule) Column - (Il) (pKa of conjugate acid) © ty © ty (9 10.95 (08 (5.33 (9 10.65 Match the column Column (Compound) Column-l (PK, values) CN) ® O oO) ass od \ * () 13.60 (ei (9) 8.80 ANSWERE KEY DPP No. # 02 (JEE-ADVANCED) 1. 8. 15, 22. 29. 36. at. 43, 44, © © © 6 7 © © 2 a 16. 23. 30. 37. 42. oO. © 4 © & © & ® 2 © ov. © %1 © 2 © 8B © & W (ABCD) 17. (ACD) 18. (AD) 19. (AB). 20. (AD) 2.3 6 2m 4 2 9 22 3 7 4 2B 6 0 * #@ 2 © 8 © *& © &% © Oo 8 O 7 © 8 O % O © Ar; BO +P: OC) >a: O) +s A>4a.t);@>p.9);(C>p.48,t);Oors,t) (A>4,8);8>p.8); (© 31,8); >4,t) Apt: @ors:Oopat; Qorpat I ———————— Educating for better tomorrow | FearpreeyaoS TO SET TAO [PEE S555] CIN: UBDIOIRIZ00TPLOUDAOZS PAGE NO.

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