IN Resonence” Educating for better tomorrow TARGET : JEE (ADVANCED) 2017 Course : VIJETA & VIJAY (ADP & ADR) Date : 19.04.2017 TEST INFORMATION DATE : 23.04.2017 Syllabus : Full Syallabus DPP Syllabus : Organic Nomenclature, Isomerism, Stereoisomerism, GOC, POC, Tautomerism, Acid & base DPP No. #3 Comprehension ('-1' negative marking) Q.26 to Q.33, (3 marks, 2 min.) [24, 16) the (d) sample ? » SCY 7 be ‘Sum of total number of chiral centres (x) and total number of pairs of enantiomers (y) for following structure is . (A)2 (B)3 C4 5 (4 es os (os 0; Oo 9 ° ° oO Oo . wy. . (A)P>Q>R>S (B)P>S>R>Q_ (C)R>S>P>Q_ = (1) S>R>P>Q (A)2 (B)3 (C4 (O)1 ate Office + OG Towe, AG & 52, IPIA, Neat Gly Wall, Jhainwar Road, Kota (Raj) 524005 PN Resonance rare10. ns Me, Ae on © w (A) 1-4.11 0 :11-6.87D (®)1-687D;11-4.11D (©)1-4.41D 5-411 D (©)1-687D;11-0D Which of the following compound is most stable? CHe ‘AcO’ AcO” Which of the following has lowest pk, value? O Oo & pee @O-+O) © COO © HS MeN : : NMe, naphalene Reason for high basic strength is (A) Resonance (® Steric inhibition of Resonance (C) Ortho effect (©) Hyperconjugation Among the following, the most stable isomers OH a OH OH — ‘OH oor oZt~pon oLtr~pon ota The element(s) of symmetry present in the following molecule isfare cH 4 4 oH vy, ch oH, H (A) Altemating axis of symmetry (©) Plane of symmetry (©) Axis of symmetry () Centre of symmetry Educating for better tomarrow Cor’42° 43° 140 18" 16" ae Which statement about the following equilibrium is False ? 0K: tbutoxide eke (A) The equilibrium favours the products (B) t-Butoxide is the dominant anionic species in the equilibrium (©) Wateris the weaker acid than t-butyl alcohol (©)t-Butoxide is stabilized by resonance Which of the following structure has correct IUPAC name Me. Me a oO 2-Bromo-5,5-dimethylcyclopent-2-en- Br No, CHO. ®) 6-Methoxy-1-nitrocyclohex-t-ene 2 ofl 6-(Cyclobut-2-eny)hex-2-ene Br. © I 2-Bromo-6-nitrosobenzenecarboxamide Correct statement isfare regarding carboxylic acids having molecular formula (C,H,0.) containing aromatic ring, (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)Allthese Toluic acids are weaker acids than benzoic acid (D)All these are weaker acids than H,CO,, Select the correct staternent(s) about the following reaction (0 (R) Thalidomide derivative a (A) tis an isomerisation reaction. (®)Itis aracemisation reaction. (C) The reaction is passing through the process of enolisation. (OD) landil are tautomers. Mark the compound given below which have atleast one meso stereoisomers. (A) Cyclopentane-1, 3-dicarbaldehyde (®)Hexane-1,2,3.4,5,6-hexol (C)2,3,4,5,6-pentahydroxyhexanal ()2,3-Dihydroxybutanedioic acid By CHs Choose the correct option/s according to the given compound. cH 1 (A) Total stereoisomers are five. (B)All stereoisomers are optically active (C)All stereoisomers are optically inactive. (D) Four stereoisomers have plane of symmetry & one has centre of symmetry Resonance’ Educating for better tomarrow18° 19" 20° ae 22 23. 24. Which of the following are (configurational) enantionmers of (P)? P)= 4 cH, ch, cH, ch. cH, Cr a 4 4 1 H a H on ” a Oe a Oe 2 O _ cH, cH, CH, a The correct statement about the following compound is : We SS (A) Ithas four enantiomeric pairs, (8) Ithas six diastereomers, (C) Ithas two optically inactive stereoisomers. (D) Ithas only one enantiomeric pair with cis and trans configuration about the two double bonds. Which enamine of molecular formula ©,H,,N can exhibit geometrical isomerism. Sy 2 ® = ©>ns © Which of the given statement(s) about N, O, P and Q with respect to Mis (are) correct? a " “ / ul CH, CH, ; H7~on HHO Ta CH AS 4 4 Ht He 4 He HOH H \ : " a & M N ° W a (A) Mand N are non-mirror image stereoisomers (8) Mand O are identical (C) Mand are enantiomers () MandQ are identical Select the correct statements (A)Aracemic mixture can be distinguished from a meso or an achiral compound by optical resolution {®)dand / stereoisomerof the same compound are enantiomers of each other. (C)A chiral compound may or may not have assymetric carbon. {) There is no obvious correlation that exists between the configurations (R or S) of enantiomers and the direction [+) or )] in which they rotate plane polarised light Statement-4 : Trihydroxyglutaric 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-1 is true, Statement-2 is true; Statement-2 is correct explanation of Statement-1 (8) Statement-t istrue, Statement-2 is true; Statement-2 is NOT correct explanation of Statement-1 (C) Statement-1 istrue, Statement-2is false. (0) Statment -1 is false, Statement-2 is true. Statement: There is evidence for existence of Nrmethyacelamide in two structuraform land las shown below a 6h Pe Sond! aH fH, 1 il ‘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 (8) Statement- is true, Statement-2 is true; Statement-2is NOT correct explanation of Statement-1 (C) Statement-1 is true, Statement-2 is false. (0) Statment -1 is false, Statement-2 is true. _[ corporate Orica 7G Toon Aa & BE, PIA, Nea Oy Wal Tawar Ron, Ka oy) SBOE Resonance’ Educating for better tomorrow oes25. Meg ,H Ho Me ? OF NH O57 NH Hen to HANS bo He HT Me @) @) Statement-1; Ais optically active & Bis optically inactive. ‘Statement-2 : A has centre of symmetry. (A) Statement-1 is True, Statement-2 is True; Statement 2s a correct explanation for Statement-1 (8) Statement-t is True, Statement-2is True; Stalement-2 is NOT a correct explanation for Statement (C) Statement-1 is True, Statement-2 is False. _ (0) Statement-1 is False, Statement-2 is True. Comprehension #1 28. 27. 28. The compound shows below in the diagram, on treatment with acid catalyst isomerizes and equilibrium is Ostablshed among the stereoisomers, CH,-FH-CH-CH, where X#H or CH, x x 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% (©) 35% (©)46% (0) 54% The percentage of racemic mixture present in the equilibrium mixture is (8) 35% (8) 45% (65% (©) 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 —_(D) 20% meso, 30% dextro and 50% laevo Comprehension #2 29. 30. ‘Aresearch scholar synthesised the compound Ain the laboratory oH, Ais? Den, ‘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 5 c Reaction with NaHCO; TOO; No readlion No reaction Blue litmus red No No NaOl No No Yellow ppt Ao(NH) I No No Siver minor [Hint:A #2", Ba cy Compound Bis ° ° ° “ tk ® Chen © Q. None oa H.-OH Compound C is pee ee Educating for better tomarrow agat. Bis formed due to (A) Cleavage of C-O bond followed by esterification between COOH & ~OH present. (B) Decarboxylation of COOH group (C) Oxidation of -CH,COOH into~COOH (D)None Comprehension #3 32. 33. 34, 36. 36. 37. 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 (D) none of these A optically inactive form P is (A) Optically inactive due to internal compensation. (B) Optically inactive due to presence of plane of symmetry, (©) Optically inactive due to external compensation. (D) 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 ? oH, COOH bh, ou fo") cH NOC, 4 (2)H" td (3) be ‘ a * HC; He: C CH, OH i ‘The total numberof isomeric product formed is Whatis the numberof al he structural isomers of octane wih five carbons in ther principal chain? How many optically active compounds are possible in the following reaction? He igsnv mmenochoraton Product (S) H, Educating for better tomarrow Ca38. 39. 40. at. 42. 43. CH, 20, cx lon, + Hooc-4-coon a (Smale) (2 mole) (1-mote) How many bonds are present in compoud A? Asmallest, 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 . Br w (i) iil) : A OS (wv) w wi) HAC} CH, HO ° A 2M solution of glyceraldehyde (HOCH,~CHOH-CHO) was placed in a polarimeter tube 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 (I) and (Il) Column Column Molecule Property cH, cl (p) Chiral atom is present H (9) Plane of symmetry is present “ an Br 0. ® (@ Motecule is chiral oI () > () ch re Hy cH = (6) Centre of symmetry is present Match the column (0) and (I). Column4 (Compound) Column-II (used for separated between) (A) NaHCO, solution (P) CH,-CH,-NH, & CHy-CH,-NH-CH, (©) NaHsO,, (@) Ph-CO-NH, & Ph-CH,-NH, (©) il. HCI (0) CHy-CH,-OH & CH,-CH=O g © cH{O)-$-< KOH (6) Ph-COOH & Ph-OH ° Educating for better tomarrow DaMatch the column (0 and (1, Column()) Molecule a) ® | CH-CH, © at Column (tt) pKa of conjugate acid (08 (95.33 (10.65 (9) 10.95 48, Match the column () and (I) Column (Compound) Column-tl (PK, values) (A) Od) (p) 13.60 N ® O @e2t Cpe) (9335 oes (5) 8.80 i H ANSWERKEY DPP NO. #2 1. © 2. e 3. © 4. © 5. © 6. © fy © 8. (ABD) or (ABD) 10.* (ABD) 11." (ABC) 12." (BD) 13" (C) 14." (BCD) 15." (ABC) 16." (ABCD) 47" (ACD) 18." (AD) 19" (AB) 20." (AD) 21. @) 22. A) 23. © 24." (AD) 25." e) 26" (BCD) 7 © 2" © 29" (ABC) 30. © 34. © 32) 33.8 34.0CO«8 35. 6 3.4 7.9 33 34 40. 8 4. i 42. (A+; Bp); >a) :(0>5) 43. Aaqt); > p.a);(C>prst) | >rst) 4, A>g9;6>Ps):(C>19);O34) 48. AP): B>49);(C>pqd ; O>0, Resonance’ Educating for better tomarrow