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Carbonyl Assignment

Carboxylic acids and derivatives

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Saheb Priyadarshi
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Carbonyl Assignment

Carboxylic acids and derivatives

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Saheb Priyadarshi
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© © All Rights Reserved
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[ Exercise -1 I (Only one option is correct) 3.) TP B-hysroxy ketone AA -esermirsoaa | mate > 9 ‘Stucture of (P) is OH (ay < ‘oH 1 (A) (6) U ° ° ° DAY on Qo ° o ff 4 H-c-H 2 Gar ite — CH, 0 ° 4 DAA usu ° a) AAS (P) major product on OW ° odAnAK oO oye ° 1 j © Wy on ° (ey ne (0) None one ° (D) Wy ° LIA, 8200 o : ‘major product structure of (x) is OH CHO. (A) (8) oH cho con © (0) ‘Aldol addition can be (A) Acid catalysed (8) Base catalysed (C)Acid promoted (D) Aand B both cts A sre is AA Ns ‘Total number of aldol condensation products are (excluding stereolsomer) we @3 (oe (0)5 +) (x) and (y) are 10 ° ‘ye saint, to Product (P) Is oH & ° “ o~ » ° © o~ ° o Ho: e a 2 13. 4, 15. ovo Reagent (x) is (a) PCC. (8) Cr0,,H,SO,,H,0 (C)Ag,0,NHOH — (O)AI Ho ro (CHOH), —+ (CHOH), don HOH Reagent responsible forgiven conversion will be (A)4g,0,NH,OH (8)8«, 4,0 jc (Ol HCHO —co sent (x) + (y) (i) Oxidation number of carbon changes from (A) Oto +1 and Oto -2 (8) Oto +1 and Oto-1 (C) Oto +2 and 0 to -2 (D) None (il) Given reactin is an exampleof (A) oxidation (B)Reductopn (C)both (O)None, Compoufid which gives cannizaro reaction? (ayen,cHO (8)H,CH0 (cycH,cooH, (0) Ce Compound which gives intramolecular aldol re- action? wOre © (0) Band C both 16. RAK Product Degree of unsaturation in product is? (A)2 (8)3 (c)4 (0)5 cH, ” [Fa c.compound (Cis: ° Ln, “yah fy 9 18, This is an example of an intramolecular aldo! reaction: © a (A), 0 Product (A) is: Sp «tO dy eD 19. a. ‘Which add can be oxidised be Fehling solu- tion: (A) Malonic acid (C) Oxalic acia (8) Acetic acid (0) formic acd fodoform test Tollens test Positive Tollen’s Test Compound (A) Is 9 och, ll | (A) cH i CH. CH, (8) cH,-C-C- cH, 4 cH, o=0 (c) CH,~ C ~ CH,- CH= OCH, ocH, | (©) He C= CHe CH ty och 81% yield; Product of the reaction is “i od why why 2 CO, cnn (8) +10) ; Product (C) is HBr Progud aye “ Ne oX ok oy< 2. (A) “oO | woo KOH,e dy by “OO (8) ; Product (B) is 2. on a) AX» Ph-CH=0 KOH, a | Product (B) is (8) (A) Ph - CH = CH - Ph (8) Ph-CH = CH-CH=0 ony oO Nm ass Lowe, (B) ; Product (8) is. (A)Ph-CH= C -CH, oH, oH 1 € (8) CH-Ph(C) Ph =O) =CH -Ph x (0) Ph-CH=CH-CHEO Gem dilhalide on hydrolysis gives: (A) Vic diol (8) Gem diol (C) Carbony! compound (©) Carboxylic aca Ph-CO.H + CH,CO,H [20 9 4 (A) Ph-C-Ph (8) Ph- C-CH, (Dall © A ‘Arrange these compounds in decreasing order of reactivity for the nucleophilic addition reac- tion: a. 3B. (1) Acid chloride (Wl) Aldehyde (lit Ketone (tv) Ester Select the corect answer from the codes given ow: (A)I> > Ill> tv (B)IV> Ml >II>1 (Ch >M>I>Iv— (O)I>WV>U> MH Acetal or ketal is: (A) Micdialkoxy compound (8) a, «a-dialkoxy compound (C) q-alkoxy alcohol (0) Gem dialkoxy compound mS. Product (A) Is ° ) (8) Ht ro) (0) In the given reaction: ¢ cohen un, (x, ] willbe: (A) Only syn oxime {8) Only anti oxime (C) Mixture of syn and anti oxime (0) Secondary amide ‘Schiff's base is prepared trom: (A) Carbonyl compound and primary amine (8) Carbonyl compound and secondary amine (C) Carbonyl compound and tertiary amine {D) All of these ‘Schiff's reagent is used for the differentiation between: (A) HCHO and CH,CHO (8) CH,COCH, and CH,CHO t (©) GH, = Cf ~ CO, and GH, -C“CH-CH, (©) HCHO and C,H,CHO ” In the reaction sequence[X] is ketone: [x] _ssunetina , HOOK (CH,),-CH,-COOH (x) will be: oo “ db . “an oy" In the given reaction ke Xd a wile : CHO ©. A) (8) cH, CH, «© (0) 3 ‘0 i b-€-p Cus oer ete rence (2 (B)3 (ca (o)1 In the reaction (X) and (Y) will respectively be: (A) CH, CH, ~CHO and CH,-CH,-CHO (B) CH,-CHO and CH,-CH!-CHO (C) CH,-CHO and CH,-CHO. cH, | (0) CH,-CHO and CH,-C-CHO | cH, a1, Total number of products in the given reaction (exduding steroisomers) GH,CHO+CH,-CHO—*» Product will be (A) One (8) Three (c) Two (0) Four In the reaction: Om C0 Sus, DC will be “OOO Product of Perkin reactionis : (Aja, f-ungaturated aldehyde (8) “cyclohexyl a,fi-unsaturated aldehyde (C) B-Aryl-a,B -unsaturated acid (D) All of these The product of the reaction: wo-XLO)-crortencccoy@ [ercercoors a oy [x1 wall be: (A) GH, ~ CH = CH COOH wore, {O)-o1- - ho oD Cyanohydrin of which compound on hydrolysis will give lactic acid? (A) GH,CHO (8) HOHO (c) cH,cHO (0) CH,-CH,-CHO Acetaldehyde cannot give: (8) CH,-CHO (D) All'of these (A) lodoform test (B) Lucas test (C) Benedict test (D) Tollens test OCH,CH, compound Non formed by the scr trict Sethe (A) an aldol (B) an acetal (C) aketal (D) a hemiacetal 49, O-- (A) _co10_, (B), Product (B) is: (A) FH.-OH (8) (OH H,-OH 0,4 (C) CH,-OH (0) co? & & Which of the following will reacts with NaOI (A) CHY-C =H (B) 5 ¢ oJ om NaH,CH,1 4) LDA,CH,L Q) Product (P) and (Q) respectively is: we b&b db bb ‘Which of the following compound not reacts with NaHSO,? (Ay H- CH 0 JL ° | ote o cron: @ sins 4 (B)cH, © By + (8) Product (8) is (OycH,-0-cH, pt spec onemn-cO: K When’A reacts with 8 in presence of KOH/ 4 product Cis formed product Cis? (A)Ph-CH=CH-CHO- f (8) Ph-CH,-CH,- C-CH, i (C) Ph-CH= CH- C -CH, () None 97. Ph -CH=O+NH,-NH, 1 (A), Product (A) is known as: (A) Aldo-Oxime (C) Hydrate (8) Hydrazone (0) Phenyl hydrazone HO-CH,-CH,-CH=0—*> 5 (A), Product (A) is: (a) Y ‘OH (8) ° 9 (c) 7 y oC%, H on o 9 End product (P) of above reaction is: Dik xt » AA Clo =e (B)Major product (8) is: “cect “- 61. i CH,- C-CH,+H-c-H sm, a} major Product (A) is wha oda 0 var o80 How many hydrogen is replaced by Deuterium (Ay2 (8) 10 (c)7 (D)8 ° Aue " Find out the incorrect statement iabout the. above given reaction (A) It ts 2 nuclephilicaddition réBttion (B) Obtained product is presentin racemic mix- ture (C) Ifthe hydrolysis of obtained product give a-hydroxy acid (0) It isa electrophilic addition reaction Comprehansion : (9.62 to Q.64): Aldehydes and ketones react with one mol- ecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl Group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol Gives an acetal and a molecule of water. We study this reaction Draw structural formulas for the hemiacetal and acetal formed from these reagents. The sto- ichiometry of each reaction is given inthe prob “ Cre 4+2CH,CH,OH_"_,(P) Cyclohexanone Ethanol nC mencenoio1 = Cyclohexanone Ethylene glycol OH ° © cx Ae ‘OH cis-1,2-Cyclohexanediol Acetone Product P is . ort et “ oe ©) ort ome oe Product Qis . »OEx oCnx Product R is . wo Ie (cy On 2 s. TAI] g.__ Schiffs reagent gives pink colour with: phatic & aromatic) (A) Acetaldehyde —(B) Ph-CH. i (C) Acetic acid (D) Methyl acetate (A)CH,- C -CH, (B) CH, ~CH,- C-CH, ‘Which of the following compound will give posi- tive Tollens test I (cyPh-C-CH, (0) CH,-GH,-C -CHPh (aycH,cHo oy on Two isomeric ketones, 3-pentanone and 2- pentanone can be distinguished by: (A) L/N2OH (BN (OVCHOH,CHCH, EH-0CH, ccynacnna. (0) 2,44 on Stability of hydrates of carbony! compounds ‘OCH, depends on: (0) CH, CHA (A) Steric hindrance ‘ocH, (8) Presence of -1 group on gemdiol carbon (C) Intramolecular hydrogen bonding (0) angle strain in carbony! compound Whcih of following give positive test with 2,4+ NP? (A)OH-C-H_—(B)OH,-C-H, (©) CH,= Column it (P) An enamine will form (Q) Schiff base will form (R)Hydrazone will form (S) Product form willundergo Lassign test Column! OH “ONS on 9 ° O 7 O OH o O a O oH cl ° O 7 O Column tt (Reagent used) {P) AIOCHMe,), or HN {Q)A(OCMe,), oF Cro, (R)HPO/ 4 (S) cone. HCI et of the reaction of propanal with each o the fllowing (2) Lithium aluminum hydride {(b) Sodium borohydride (c) Hydrogen nickel catalyst (4) Methyimagnesium iodide, followed by dilute acid. (e) Sodium acetylide, followed by dilute acid (8) Phenyllithium, followed by dilute acid (g) Methanol containing dissolved hydrogen chloride (h) Ethylene glycol, p-toluenesulfonic acid, benzene (1) Aniline (CH,NH,) {G) Dimethylamine, p-toluenesulfonic acid, benzene (&) Hyderoxytamine ( Hydrazine (en) Product of part(!) heated in triethylene glycol with ‘sodium hydraxide (7) p- Nitrophenyihydrazine (0) Semicarbazide (p)Ethylidenetriphenyiphasphorane ((C.H,),?-CHCH,] (q) Sodium cyanide with addition of sulfuric acid (8) Chromic acid 2. Give structure for the products of the reactio. when butanal is treated with each of the fol- lowing reagents (2) Ag(NH,) OH then HOH /H™ (b) GH/HOH, A (©) NHLOH/UT (8) C\HUithen HOH (e) GH CHO, OH, 4 (A) CHeCNa then HOH /H* (9) CH,OH- CH,OH, H™ (h) SH-CH,-CH,-CH,-SH then Raney N/M, (i) CH,MgBr then 4,6 Gul i (k)NaBH, (I) CH,-CH,-CH-COOC,H, and 2n then H,0/H® (Reformatsky reaction) 3. (a) Arrange the follwong compounds in decreading order of K,, for hydrate formation. qa) ' ' @ i wo-XO-¢ -cH,; onOyten 3) a (») Equilibrium constants for the dissociation (K,.,) of cyanohydrins according to equation RER K, pS Se once + HN cn Cyenohydrin Aldehyde Hydrogen for ketone cyanide have been measured for a number of cyano- hydrins. Which cyanohydrin in each ofthe fol- Towing pairs has the greater dissociation con- stant? OH ‘OH wy cen den or (CH,), CON o# on (N)GH, CHEN or C,H ic H, ‘Some grignard reagents react with ethyl orthoformate followed by acidic hydrolysis to lve aldehydes. Propose mechanisms for the ‘two steps in this synthesis. o-cHcH xe RC-0-04,0H, oC * Suggest a reasonable mechanism for each of the following reactions: (OE AA oy, seen OM Sie * (CH), CCCH OCH, a (88)% Predict the organic products: (2) CH, -C~CH, + HO- CH,-CH,-NH, wm (CH,—CH,—CH,—NH, ye sem von i © Opera A synthesis that begins with 3,3 - demethyl- 2-butanone gives the epoxide shown.Suggest reagents appropriate for each step in the syn- thesis. (2) (CH,),CCCH, =, (CH,),CC CH, Br on I (CH,),CH, oon Aol (©) Overal yield ofthe rection is [=] Outline resonable mechanisms for each of the following reactions: Sovoren, LOLCHBF ge a (P Give the structure of the substance for each (of the following reaction : (2) (x) sown, i —cH, (b) (¥) Nets 10. (@ ee, CO, Each of the following reactions has been re- ported in the chemichal literature. Write the structure of the product(s) formed in each case. 9 © ne{ Seo, Saas Hy ) oth +6 Ken = [ Exercise -IV | PREVIOUS YEARS PROBLEMS Leve.-I JEE MAIN Qi Which one of the following Is reduced with zine and hydrochloric acid to give the corresponding hydrocarbon ? [ATEEE-2004] (A) Ethyl acetate (8) Acetic acid (C) Acetamide (0) Butan-2-one 1.2 Which one of the following undergoes reaction with 50% sodium hydroxide solution to give the corresponding alcohol and acid ? [ATEEE-2004) (A) Phenol (B) Benzaldehyde (C) Butanat (0) Benzoic acid Q3__ The best reagent to convert pent-3-en-2-al into pent-3-in-2-oneis- [ATEEE-2005] (A) Acidic dichromate (8) Addic permanganate (C)Pyridinium chioro-chromate (0) Chromic anhydride in glacialacetic acid Q.44 _Theincreasing dederot the rate of HCN addition to compounds A - D is - [AIEEE 2006) (2) HCHO (b) CH3COCH3, (c)PRCOCH3 —_() PREOKHs (d —(D) NOOH/Nal/H" 10. The smallest ketone and its next homologue are reacted with NH,OH to form oxime. (DBE 2005) (A) Two different oximes are formed (B) Three different oximes are formed (C) Two oximes are optically active (0) All oximes are optically active Which of the following reactats on reaction ‘with cone. NaOH followed by acidification gives the following lactone as the only product? (Dee 2006) COOCH, COOH ww ‘COOH ‘CHO COOH CL. @CL 10 ‘COOH Cyclohexene on oxonolysis followed by reac- tion with zinc duct and water gives ompoundE. Compound E on further teratment with aque= ous KOH yields compound F. Compound F is (Dee 2007) w Low ow © EO con Statement -1 : Glucouse gives a reddish- brown precipitate with Fenling’s solution. because Statement -2 : Reaction of glucose with febling’s solution gives CuO and gluconic acid. (3eE 2007] (A) Statement -1 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 corrcect expla: nation for statement -1 (C) Statement -1 is True, Statement -2 is False. (0) Statement -1 is Fals, Statement -2is True. Match the compounds/ion in column | with their Properties / reaction in Cloumn Il. Indicate your answer by darkening the appropriate bubbles of the 4 4 matrix given in the ORS. (DEE 2007) Column | A) CGH.CHO (@)ch,CacH an" (opt Column (®) give precipitate with 2,4- initrophenyinydrazine (Q) gives precipitate with AgNO, {(R) isa nudeophile (5) is involved in cyanohyarin formation 12, Match the compound in Column | with their characteristic test (s)/reaction(s) given in Col- ‘uma Il. Indicate your answer by darkening the appropriate bubbles of the 4.4 matrix given in the ORS, (EE 2008) Column! HN NHC fai ie LX coon ove md ©) on Qn in vo, Column IT (P) sodium fusion extract of the compound ives Prussian blue colour with FeSO, (Q) gives positive FeCl, test (R) gives white precipitate with AgNO, (5) reacts with aldehydes to form the corre ‘sponding hydrazone de rivative Paragraph for Question No. 13 to 15 A tertiary acohol H upon acid catalysed dehydration Gives a product I. Ozonolysis of | leads to compounds 3 and K compound 3 upon reac- tuon with KOH gives benzyl alcohol and @ com- pound L, whereas K on reaction with KOH gives only Ba. (DEE 2008} 13, 4. 15. Compound H is formed by the reaction of Ph H, © A, + PRCH,MgBe Ph: H, © A + PRCHMgBr hr H 9 + Ph 4 Mg8r ° (0) ‘The structure of compound | is Pn na) “ = ®) ~. " mW hm oo © (0) =< " rT." 4 The stfuctures of compounds J,K and Gypncocn Poo nce, (A)PRCOCH, ,PRCH,COCH, and PRCH,COO-K* (8) PhCHO, PRCH,CHO and PhCOO-K> (C) PRCOCH,, PhCH, CHO and CH,COO"K* (©) PRCHO,PhCOCH, and PRCOO'K: Paragraph for Question Nos. 16 to 18. 16, ‘A carbonyl compound P, which gives positive lodoform test, undergoes reaction with MeMg@r followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl com- ound R which undergoes intramolecular aldol Feaction to give predominantly S. (32 2009) pti gp sng arn 2 a anKo te ‘The structure of the carbonyl compound P is : OD, OX 17. 18. ©) Com ©) eat e ee et The structures of the products Q and R, re- spectively are ° Me 4 OS) f come ™ meme Me*Me ° H (8) . cHO Me ~N H (ey . cHO et Me ie Et te ° cH, (0) . cHO. Me eC ‘The structure of the product S is : “ co ) On Me le Me 9 Me «c) (D) je Me Paragraph of Question Nos. 19 to 21 ‘Two aliphatic aldehydes P and Q react in the presence of aqueous K,CO, to give compound R which upon treatment with HCN provides ‘compound S. On acidification and heating. S Gives the product shown below (DEE 2010) HC H He ‘0 19, The compounds P and Q respectively are = cH, | on ond 4 ond ff ° a. HOS UO, Mucrt Hc NOH (CA yy, HC ‘Son Five isomeric para -disubstituted aromatic com- pounds A to E with molecular formula C,H,0, were given for identification. Based on the fol- lowing observations, give structure ofthe com- pounds. ([38€ 2002] () Both A and B form a silver mirror with Tollen's reagent; also, Bgives a positive test with FeCl, solution (iI) C aives positive iodotorm test. (ill) Dis readily extracted in aqueous NaHCO, solution. (iv) E on acid hydrolysis gvesi, 4- Gihydroxybenzene. GH, 9GH,A+ (0) “ ®) Linea (D) soma , (E) (#0) (A) SEES (F) + (G) BAe HCOONaY IPalcoho! (0) is isomer A. E gives negative test with Fehling solution but gives lodoform test F and G gives Tollen’s test but do not give lodoform test. Identify A to G. (DEE 2003) Give major product A, B,C and’D in following reaction sequence. (DEE 2004) CHCl EOL. (ny AP NeDEVEROH, DI ™ Ui) PRCHO/A » -SOCk AEs (iy CHW Which ofthe following disaccharide will not re- duce Tollen’s reagent ? (DEE 2005) cHOH cHOH Hog 0 4 Ho “ o 4 OHH oH tow,c (2 CHOW HOF-Q OH eH +) 4 w@ het cy 0) oP Identity (x) and (Y) (ee 2008) In the scheme given below the total number of Intramolecular aldol condensation products formed from ¥ Is (Dee 2010) OO [Answers —=*@Yds Exercise-I 1B 2c 3.0 4.8 5.0 7.8 gic 30 10.¢ a 12. 14.8 15.0 16.8 7A 1B 13.0 ane 2A 23.8 24.8 25.8 26.0 28.0 2A 30.0 BLA 3c 33.4 35.8 36.8 37.8 38.8 39 40.0 420 aA 4 45.C 46.¢ 47.8 43.6 SOD SLC 52.0 53.0 54.6 56.4 57.0 58.8 59.¢ 60.8 61.0 6.8 eB Exercise-II 160 2.AB 3.ABCD 4.48 6.ABCD 7.8.6 aA SABC 10.40 11.480 13.0 14.¢ 15. A-R;B-Q;C-Q;D-P 16. APS 8-995; C 3Q,5;D-4R,S 17K PB Q;C Ri 4S Exercise-III 1. (@)CH,—CH,—cH,—o# {b) 4,=Ch,—cH,—0n (0. CH,-0h,—cH, oH rh oH on (0)0H,-CH=CH cH, (@) CH, —CH,— CH —cacH (90H, —cH,—CH— Ph OHM-CH~ cH 00H, em Hc cKO] (0) 4,-Ch, Che NP Ot 0) 0, -cH,—cH = i —cH, ()C-C-C=N-OH (CH, —CH, CH= NN, Hy (m) H,-c4,—cH, (6) P-Nitro phenyt hydrazone (0) semi carbazane on (®)CH,—CH,—CH=cH—cH, (@) CH,—CH,—CH CN (9.04,-04,—C0,H 2 (@)C-c-c~ C—on (©) CH,-CH,-CH,-cH (.c-C-c-C—C=N—OH OH on (ccc bmn (e) Ph-cH=c-cH,-CH, (nc—c—c—cH—omcHt y 0 (g)C=C=C—C<_, (h) C—C—C—-C (i) 2° alcohol on ) Cyanohydrine (k) 1° alcohol (0,-cH,-c4,— by-PHo0n e r r 3 (a)3>2>1>4 (©)()(CH),CCN (NGA, CON cH, 4. R—Mg—x (CH,),Cs 5 OA 208, tome j -cH.0cn, — (cn)c-C-cHocH, i 6 (@)04—cH —NH—cH,—cH,~04 oLQace+O-bom | N’ ' h cH, 7. WON Begins HY ‘Nace 10, Exercise-IV (LEVEL-1) hoop 2 8 3 0D 4 B & D Exercise-IV (LEVEL-2) RhoA 2 © 2 C 4 A & C 6C zB 8 ¢ & A 1 Cc 11, A-P,QS:B-+QR;C-2Q.R,S;0-+QR 12, A-R,S;8-P.Q:C—P.Q,R;D—PS (OR) A-R; B—P.Q; C- 38 mM A 1S. DO 1 BOI A 1 B18 2A 2 OD RR; D—P -CH= CH, CH.-CN LO .Me,C—CH=CH, #1, Me, c —CliMe,+Me,C—CH-Me CH= _ ‘ i : aon oy oy q a a (8) © Pane 9 O-Gih (4) C2228 cHO*Me,c-cHo NOH __, soa (F), ©, (0) < Go HCOONa+Me,C-CH,0H(1°alcohol) In structure (P) both the rings are present in acetyl form therefore it will not hydrolyse in solution that why Tollen’s solution connot react with this. In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed In solution it can reduce Tollen’s solution. o I 26. (x) (1) CH,—C—(CH,),—CH=0 a Carbonyl compound option sol.2 Ans. sols Ans. @ « He f-H have no a H 89 do not show aldol Roe ° ©) @) & Seah 01.6 Aldol addition are proceed in presence of Base catlyst as well as acid catalyst. ‘Ans. (0) sol.7 Yeo ant, AL ans. (8) sols, 4° y—™ boch aldehyde having u ~ H So 4 product Will 6é formed in which two self and two cross. Product won we 9 Ne* oi NaOH ~O-O ” ” Ans. (0) a . . ~ PCC. ‘Oo u(oy~™ 2+ (OY P.C.C. -+ Pyridine Chloro Cromate s0L12 CHO porn (CH-Om, —SEHO_, (GH-oM, meO.NHon” “T CH-OH cu" -OH ‘Ans. (D) HoHo -COHNBOH, 6 oP Na? + CHL-OH vaaten NO ° soLi3, onsen fe Recseton ans. (C) ‘201.14 Corbonyl Comp having nou ~ H gives cannizaro Rx ans. (B) ‘501.15 Intramolecular aldol reaction - ; wy on? ans. (0) 1idol Reaction) (Intramolecular Ans. (A) He -on HO SS Ho co, sol.19. 5 cu" —+ on" ‘Ans. (0) Positive Tollen Test Ans. (C) oO oe Q,/2n Cree On KOH COONa aa —aas ‘CH, OH Ans. (A) “ HCHO, KOH Ans. (8) Ans. (0) sot29 i Decreasing Order of reactivity towards N.A.R. a> a > one > CHF oot 8 ans. (A) cH CH. OCH, 301.30 Npeo + zonon \ 4 Cr 7 Noch, peat CH CH. OCH, =O + 2CHOH ——+ c. cH CH, 7Nocn, etal Ans. (0) Ans. (A) cH, a 901.32 - H =N ETH oF Mean OF CH He on bros ans. (a) 8 seis oN Noone caer Cove a Ans. (A) 201.34 Schiff’s reagent is [P rosanilline + HCI + SO, ] which is used for different b/w Aldehyde or Ketone. Ans. (B) 50% KOH 2 sot37 7 FO 0,-cH-on + i oO Hydride shift is RDS step in cannizaro Rx" so Third order of Ru Ans. (8) on l satse O8=0H0°0 0H, -cH0 MO, od g cro “ sc *) ” CH, ans. (8) ° sol39 CH.CHO + cH -cHO AO aati 9 w” | noa-H (Cross Product) CH,~ CH = CH= CHO (Self Produa) CH, - CH = CH - CHO Ans. (C) mn Dee One atts ‘Ans. (D) + ot-g-o-g-cn, £Hc08 Na, Pr gi pt coon § 3 Pte arenes omaha) Ans. (C) en -crco8%e ai ~-©> 20 enon ttoy ote ()) onc bo boron ‘sol.42 1 bn |v 3 r0-(O)- err cnoe én, Ane D #0143 Cross Cannizzar Reaction HCHO+Pn-CHO _COH OHEHCOOPNa ® Ph — CH, -OH This is Redox Reduction. ‘oxdation| reduchon ane a 0h46 CHH,- CHO IAg (NHJ JPOH? CH, COOH + Ag CH,-CHO __H__ Ch, CH,COOH + Agi HCOOH _H_,H,0+ CO, + Agi Ans ° i Po. 0145 —C-NH [D-pomon i ° cH, CHL LOH XN IN OH . 01.46 C=O+HCN ——> —. _ Ho New 4 AS coon ‘801.47 CH,- CHO ——> negative Lucas test Ans B &y\ wl \ 0148 So ptr Oot Neon on — Ans-D 801.50 compound in which (cH-¢-] group Is present will react with Naol (NaOH + 1,) ° Ans D ° Wl ° ' Natt cH es sot CY = % WACK, fl ° ots JL, nasc;—+ Ne Fan (due to srr hindrance) Ans-D a | 0=S=0 18 8 ‘801.53 CH, OH + —> &,-0- CH, —> cH, sol54.A KOH, JA 3 a> BAR (Aldol Condensation) 8 SOK, pron, -on + Pn—c- BR j PhCHO (Connizaro Reaction) | CH-6-CHr Ph-G—H OMA + Ph oH CHEE “E-, ° ° ° Ans-C X con 4 PhCH = N— NH, H soiss PhCH “eR H-WH > |, Hydrazone Ans B 1KCN 801.56 HO - CH, - CH, - CH = O- 2H 3Ho 43 ‘OH ° Be = ts Ho cH, - cH, - cH on HO- CH, -CH,-CH cH ¢ on Ho 4 = AS Ho-cH-cHecH S| HOCH. d f é OFETAOT 01.64 (8) | loca, ™, cydohexanone _ethytenegtycot [—enacina | (oe more an one option coect_] ‘80.1 Mixed ketone (Aliphatic and Aromatic) 9 ut Pn-G-cH, I 1 . cH C—CH,—Ph amas ans = CD CH-CH-6-CH-CH.-CH, ——* Negative ladoform test 0k? o sree List, an Ponte locolorm est b oN oven Z,\tons Ans (A,B) S014 Aldehyde and ketone give positive Test with 2, 4 Dinitrophenyl hydrozine. Ans (AB) gals. Aliphatic way ‘and a-hydroxy ketone give red ppt with Febling solution. tots niphetiandvomatieidhyde give Hive miror wih Tole regent Ans - A, 8/¢,D on | foL7 carbon comp which have 2-H sve aldol Ran H=C-H—nou-H CHrG—CH, —> nowt ch Ans 8,C SOLS schiff's reasent __, [P - rosaniline + HCI + SO,] R- CHO —_** , Pink Colour Ans A 019 Aldehyde, hemiacetal gives positive poller test Ans- A, B,C ‘801.10 Ph - CHO + HCHO Ge sts, CH _ cH. OH + COP oxidation of HCHO and reduction of PhCHO Ans-A,D Con. KOH, mesic + of solid red¥ced oxidi¥ed "ed0x reaction PACH, - OH + HCt ° ‘cross cannizaro Run Ans A,B,C, D RY RA wolaa | DCrO+HN-OH PHeAs, | Yo#N-oH \oenncme gent as = =a hydrogen show (G.!) ans-D sol.14 one ono 0 OC = O~On! ~ ~ Ans C vs cits ch ono NBL cH «cr cH 04 085 (A) (All alcohal) P CH=CH +HN-Py H+ cH, ten Pn * -HO (Shift base) CHAN CH, gg >eASEBN- 1-04 —9 oe cho \ Cee ON Sata He “) OCH oR (d) R- CHO + 2R- CH,—OH o Wa Nocn Ans (A »RiBE QC QiD > Py ° “ai Orta) on M100, 3 O--O (OH a oO cones cs Ans A+PBIQC4R DS, SUBJECTIVE QUESTIONS (Exercise Sold UAH, (2) cH,-cr,-clo LAIH,, cr, -ci,-cH,0H Propanat AIH, reduses eldehyde into alcohol. (0) CH,-CH,-CHO _N2BH, CH,-CH,-CH,-OH NaBH, reduses aldehyde into alcohol (0) O4,-CH,-CHO TH CH,-CH,~CH,-OH (Reduction) ra (2) cnc 84 +6 Hat—oen, cH, -cH-cH 8 3 Obiat ho a(t CH HGH, OH (6) CH,-CH.-6H + Na-C=EC-H—eCH,-CH,-CH-CmCH () CH.-CH,-CH=0 + Ph-li —SCH,-CH.-CH-Ph u fro CH,-CH,-CH-Ph bx CCH OCH, H7Socn, Acetal @) CH CH eHED + OH, -N-CH, EES CH,-CHGH-N-CH, Henne OH GH, OHH | CH,-CH, CH: (9 CHi-cH-HCEO. +: NHOH keke tial OH (y) CH-04,-CHeO + HN mala “gel OH | CH,-CH, CH=N-NH, watt ™ Kishner CH,-CH,-CHO-SEEESE» cH,-CH,-CH, owe CH,-CHCH=N NH, I 9 or-on-enfo + spe O)-0. ps0 oxarcien (10 P-nitropheny! hydrazone 9 I (CHy-CH,-CH0 + HIN-NH-C-NH, (0) 9° u (CH,-CH,-CH=N-NH-C-NH, ‘Semicarbazone () CH,-CH,-CH=0 + (CH,),P*CHCHy A aay nclecen), cH, (O=P(Ph),+CH,-CH,~CH=CH-CH#— Betaine 224 7 (q) CH-CH-CH=0 + Hien 5 ccna" Cyanonyarin Cromic 204, (6) CH,-CH,~cHo S205224, cH-CH,-COOH $01.2 (a) CH,-CH,-CH,-CHO + 2 Ag(NH,), + 30H —» CH,-CH,-CH,-COO+ 2 NH,+2H,0 (Toltentest) | ? CH.-CH,-CH,-COOH ) CHCl eH-cH (ot cH,-cH, éo10 CH\-CH,-CH,-CH=0 u CHO CHO t Sp th CH.-CH,-CH-C-CH,-CH, (CH,-CH,-CH=C-CH,-cH, ~H.0 ba 4 (©) cH,-CH,-CH,-cH=p + HN-OH—* + CH,-CH,-CH,-CH=N-OH (d) CH.-CH,-CH, A en Hector gHecot O-u hen WOH + H.-H, CH -EH-CH, OH cron gen-cno Spence ‘4, * | HOH pnact=o'|or? © s cHacH,-e-cho 44 cH,-cH, { =H nese CH-Ph Prec en cr-cH.-c-cHE + cHmcNa—scH,-CH-cH,-cH-Ce CH 1 ‘ONa | CH-CH,-CH,-CH-C=CH oH Crt (9) CH,-CH,~CH,-cH: cn, 8 OFC, 0m HOT cH, (9) CH,-CH.-CHL-E —) renecn-cn- oY H faney mf Hs: -) + CH-CH,-CH,-CH, HS" oe +.CH.-Mg Br —>CH,-CH,-CH.-CH-CH, Ob ger HOH| H” CH,-CH,-CH,-CH-CHy (i) CHi-CH,-CH, ee ae" (Q) CH,~CH,-CH,-CH=0 + H CN——>, CH,-CH,-CH,~¢ Ny (0 04,-cH cH eho 8M cnc, -CH,-CH,-OM . cnc dn-coocn, 22+ cH,-CH,-GH-CO0C, Hy 0 2R-er & 2 CW -CH,-CHGHAO + Br - Eno pH-COOCH oH, oH, cH, cH, re I cH, cH i CH=CH -CH =EH-CH-COOCM, == CH-CH “CH GH CHG no Ozner COOC.H, oH Sol.3 (2) Because decreasing order of -1 effect of following compound is = -NO, > ~ Cl > ~ C.H,> ~CH, So decrasing order of Keq for hyalrate formation O>@>@@ {b) Due to formation of stable carbocation O-CH,-CH, 0-CH,-CH, 1g, 20 t emg’ HRoociner se | RERig-X—> R-C-OCH,-CH, + MI Oo cr, 0-CH-CH, 4 Sols eeny orthotormate fad R-C-H i o (CHC C+ CH, - OCH ° sols we GE ob tsa eoicos + CH,-CH-H- 0m,-CH,-081 Hy wO- o, ere een Ot OH + CHCl, 19, ane Sol.7 (a) OH'78r, , HY/NI , NOOH SOLB (CH,),COK == (CH,),CO™+ K™ 9 H,-CH,-CH, + (CH,),CO” Aten teecton me ° ° q Lou, me OO, Ow en, 10 © Cm oO ° 9 GH, 4 CH, (by 1H, _xOH y, 9 “i. CH, + HM, HOH or? taf ‘i outs PREVIOUS YEARS JEE MAIN ] 1D on = 0+ 2n+ Hcl cH,-c, | CH,(-CH,)-CH, Butane 2.8 Which have no of carbon undergoes -+ Acid + Alehals 3 c-c-c=c-c Pomme c-e-Cc-c § a. 5 + KOH cH, _ cH, a = + KOH ° (CC tever I JEE ADVANCED ] Loa cH,-ch,-cH,0n IL, cH,-cl,-cHo oe CH,-CH,-CH=NHHCONH, —_2Ag, + CH,-CH,-COOH +Ha+Ho Sher 2 ¢ Ho ORC (Q—<0) HO On co naonsicon| cameras eaten Be OcocH, ra CH= HOt cH CH REO” ‘CH Touts cH, - C- Hy No Fehling reaction pcocH, ZS a “Econ 7 cH, |» tomer (CHy-CH,-CHO. CH,-CH,-COO™ +ve Fehling solution soc CHO creoy, SI * ch,co Meo [oscoon cooH +.cH,cooH Me & ¢ CH, = CH, = C= CH, |:mon coach,“ CH,-CH,-COOH 2B cH, cH, ‘p= 0 H,N-OH—» =N, cay OH *, Nef cH cH, Hy, =O HN-OH> YE eN cH, chy cH, ch, syny anti Son s. 10. aa. 12, to wf ow a ove te CHO a a 282) cr0 c T A>PQS:B > QURC +URSD + GR (A) GH,CHO + NH, NHCH,(NO,), \ GLCH=N. NHC HNO), 2/4" dinitrophertyinydrazine (©) CH.C#H @) (cyen" (QXRVS) or (avai) A-R,S;B—P,Q:C—P,QR;D—P,S (OR) A—R; B—P,Q; C—P,QR; D—P_ pr git ma = ower ore ee Bea 1 oud Sp = PRcH=0 k= pn-C-cH, 3_xOM_, PRCHLOH +L L= Phcoo” 13. 15. 16, 8 2. 2B 8 a D B42 A te 9 Mey 4 fe'Me ne 9 CH ow Bano cHo | Me eM . a D $8 Gg Me,C—CH=CH, —""_, Me,C —CHMe, +Me,C—CH-Me a “ 6) ©) ale. KOH (122222 cHO+Me,c-cHo NAOH __, CF) (G) HCOONa+Me,C-CH,OH(1°alcohol) come ‘OOH \-CH=CH, O Re) Hy Ht 25. 2. HCH, In structure (P) both the rings are present in acety! form thereforeiit will nét hydrolyse in solution that why Tollen’s solution connot react with this. In structure (Q) one ring present in the form of hemiacetal. This will hydrolysed in solution it can reduce Tollen’s solution. ° t 0 (1), CHy—C— (CH) —CH= 0 tay tse (only 1 product)

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