Alcohol, Phenol & Ethers Carbonyl Compounds

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1 lcohol, enol & Ethers arbonyl ompounds Dr. Sangeeta Khanna.D 1 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

2 Test Date: Level II lcohol, enol & Ethers and arbonyl ompounds RED INSTRUTINS REFULLY 1. The test is of 1 hour duration. 2. The maximum marks are This test consists of 36 questions. 4. Keep your mobiles switched off during Test in the alls. Section (Single orrect hoice Type) Negative Marking [-1] This Section contains 6 multiple choice questions. Each question has four choices ), B), ) and D) out of which NLY NE is correct. Marks: 6 5 = What is the product (B) of the following reaction sequence? Mg Et 2 ; + 3 (1) Et 2 (2) 3 B Mg Mg Mg Sol. ; Mg 2S 4 B(Minor) + (Major) 2. 2 D D Identify, B,, D from given numbers (1) NaB 4 + D 2 (2) 3 (3) NaBD (4) 2 N 2 2 (5) (6) (7) (8) 2 I 2 /Zn(u) B D B D a b c d Dr. Sangeeta Khanna.D 2 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx 2

3 K 2 r 2 3, 7 Lil , 3 The molecule in the sequence reaction is: D Sol. K 2r L BF 4 The product of this reaction is a. + b. + + c. d. D Sol Bulky electrophile will be attached to para position only Dr. Sangeeta Khanna.D 3 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx 3

4 5. The major product(s) of the following reaction is(are) aqueous 2 (3.0 equivalents)? S 3 S 3 (P) S 3 (Q) (R) (S) a. (P) b. (Q) c. (R) d. (S) B 6. In the following reaction sequence V and W are, respectively Q 2/Ni V + V l 3(anhydrous) 1. Zn-g/ 2. 3P 4, W a. ; and Q V W b. Q ; 2 2 V and W c. ; and Q V 2 W d. Q ; V 2 and W Dr. Sangeeta Khanna.D 4 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

5 Sol. Ni/ 2 Zn(g) +, SETIN B (SSERTIN & RESN) Negative Marking [-1] This Section contains 7 multiple choice questions. Each question has four choices ), B), ) and D) out of which NLY NE is correct. (7 4 = 28 Marks) (a) If both assertion and reason are true and reason is the correct explanation of assertion. (b) If both assertion and reason are true and reason is not correct explanation of assertion (c) If assertion is correct but reason is incorrect (d) If assertion is incorrect but reason is correct 1. ssertion: enol is more reactive than benzene towards electrophilic substitution reaction. Reason: In case of phenol, the intermediate carbocation is more resonance stabilized and ring is more electron rich than benzene. a. (a) b. (b) c. (c) d. (d) 2. ssertion: hange in colour of acidic solution of potassium dichromate by breath is used to test drunk drivers. Reason: hange is colour is due to the complexation of alcohol with potassium dichromate. a. (a) b. (b) c. (c) d. (d) 3. ssertion: Ether does not form peroxide in aqueous medium Reason: Polar medium will slow down the formation of carbocation. a. (a) b. (b) c. (c) d. (d) 4. ssertion: Kolbe s reaction of phenol with 2 in presence of aq. Na followed by acidification gives salicylic acid as a major product. Reason: It is a nucleophilic substitution reaction. a.(a) b.(b) c.(c) d.(d) Sol. It is electrophilic substitution 5. ssertion: ldehydes can be easily prepared by the reduction of carboxylic acids with Lil 4. Reason: In going from to group oxidation number of decreases. a. (a) b. (b) c. (c) d. (c) D 6. ssertion: R fails to give pure ketone with RMgX but with R 2 d pure ketones are obtained easily. Reason: Ketone formed with RMgX further reacts to give ter-alcohol but no such reaction with R 2 d. d is less electropositive than Mg. a. () b. (B) c. () d. (D) Dr. Sangeeta Khanna.D 5 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

6 7. ssertion: Formation of oximes is maximum at p 3.5, this decreases with increasing or decreasing p values. Reason: t this p; \ / \ / is converted to conjugated acid which is more electrophilic and reactive. t lower p; 3 N + is formed unable to react. t higher p; no protonation of a. (a) b. (b) c. (c) d. (d) SETIN (Paragraph Type) Negative Marking [-1] \ /.. This Section contains 9 questions. Each of these questions has four choices ), B), ) and D) out of which NLY NE is correct. 9 4 = 36 Marks omprehension 1 arbonyl compounds shows two types of important properties: nucleophilic addition & acidity of hydrogen atoms. ldehydes when treated with alcohols form first hemiacetals by nucleophilic addition in the following way R = + R (i) R (ii) R R R R R R R R R ( 2) (II) (I) 1. In the above reaction, which of the two cations is more stable? 2. a. I b. II c. Both are equally stable d. None is stable B B ompound B is a b. c. D / d. \ / \ 3 2 Dr. Sangeeta Khanna.D 6 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx / \

7 3. S 1. S 2. Ni, 2 Z; Product Z is omprehension 2 lthough epoxides do not contain good leaving group, they contain a strained three-membered ring with polar bonds. Nucleophilic attack opens the strained three-membered ring, making it favourable process with the poor leaving group. + + Nu This reaction occurs readily with strong nucleophile, and with acids like Z, where Z is nucleophilic atoms. Reaction with strong nucleophile Reaction with Z 4. Find out correct product of the reaction: 3 N/ 2 S N Nu leaving group Nucleophile opens the 3-membered ring B ? What would be the major product of reaction? Dr. Sangeeta Khanna.D 7 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

8 6. 3 = = 2 (1 equivalent) () Major Find : 3 a. b. 3 = 2 c. d. B Sol. Electron rich alkene is more reactive for epoxydation Paragraph 3 The aldehydes and ketones undergo a number of reactions due to the acidic nature of -hydrogen. The acidity of -hydrogen atoms of carbonyl compounds is due to the strong electron withdrawing effect of the carbonyl group and resonance stabilisation of the conjugate base. (i) ldol condensation: ldehydes and ketones having at least one -hydrogen undergo a reaction the presence of dilute alkali as catalyst to form -hydroxylaldehydes (aldol) or -hydroxyketones (ketol), respectively. This is known as ldol condensation. (ii) ross aldol condensation: When aldol condensation is carried out between two different aldehydes and/ or ketones, it is called cross aldol condensation. If both of them contain - hydrogen atoms, it gives a mixture of four products 7. Which of the following is the final product in the following reaction Na (aq) (P) 3 a. b. 3 3 c. d Sol. arbonyl compounds containing -hydrogen atom give aldol condensation. 8. compound possessing -hydrogen atom, in the presence of dilute alkali forms -hydroxy aldehyde. This product on heating with dilute acid forms an unsaturated crotonaldehyde. The compound is a. 3 b. 3 2 c. 2 = d. Na, dil.acid Sol y droxy butanal 2 rotonaldehy de Dr. Sangeeta Khanna.D 8 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

9 9. Which is most reactive in ldol condensation a. b. 2 N 2 - c 3 d. 3 3 B Sol. ldol ondensation is given by compounds containing - hydrogen, Electron withdrawing group favour this condensation SETIN D (More than ne nswer Type) No Negative Marking This Section contains 5 multiple choice questions. Each question has four choices ), B), ) and D) out of which ne or More than one answer may be correct. 5 5 = 25 Marks can be converted to 3 2 N by the following reactions: a N b LiB 4 Ts KN S2 c. 3 2 d. 3 2,D 2. Which of the following reduction methods cannot be used for preparing an alcohol? KN 3. a NaB 4 b Lil 4 c Lil 4 d Ni,D onc. I Mg, ether B (Excess) 2, / 2 KMn 4 D a. b. B is c. d. is I I,B,,D 4. B and xymercuration-demercuration, and acid catalysed hydration will not give the same product in 3 2 is D is 3 3 2,B,D Sol. yclohexene only gives same product Which of the following would give tertiary alcohol when it reacts with an excess of 3 Mg followed by hydrolysis a. b. c. d. 2 =,B, Dr. Sangeeta Khanna.D 9 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

10 SETIN E (Matrix Type) No Negative Marking This Section contains 3 questions. Each question has four choices (, B, and D) given in olumn I and five statements (p, q, r, and s) in olumn II. ny given statement in olumn I can have correct matching with one or more statement(s) given in olumn II. 8 3 = 24 Marks 1. Match the column (ne or More than ne Match) List (I) onversion List (II) Reagent used () 3 = 2 (p) L 3 = (B) 3 = (q) ollin s Reagent 3 = 2 () R = - (r) Ni + 2 R (D) R R 2 (s) NaB 4 Sol. q; B p, s; r; D p, r, s 2. Match the column I and II. (Single Match) olumn (I) Reactant olumn (II) No. of moles of Grignard Reagent used. () Mg Et Et 3alcohol (p) 1 (B) () (2) Mg 2 3 3alcohol (2) Mg 3 3 3alcohol (2) (q) 2 (r) 3 (D) (s) 4 Mg + Sol. r; B q; p; D s 3. Match the compounds/ions in olumn I with their properties/reactions in olumn II. (More than ne Match) () 6 5 (p) Gives precipitate with 2,4-dinitrophenylhydrazine (B) 3 (q) Gives precipitate with gn 3 () N (r) Is a nucleophile (D) I (s) Is involved in cyanohydrin formation Sol. p, q, r, s ; B q, r; r, s, q; D r, q () 6 5 given Tollen s Test, DNP Test act as both nucleophile & electrophile (B) Give white ppt with gn 3 and is a nucleophile () N + g + gn (D) gi ppt; Nucleophile White ppt. (2) 3 alcohol Dr. Sangeeta Khanna.D 10 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

11 SETIN F (Integer Type) No Negative Marking This Section contains 6 questions. The answer to each question is a single digit integer ranging from 0 to = 30 Marks 1. ow many ethers are possible of molecular formula 5 12 (only structure) which will give 3 I as one of the products when treated with I(aq.) (one equivalent)? Sol ; ; ; 3 3 will not form 3 I, it give tert.butyl iodide by SN 1 reaction If the I.U.P.. name of compound is as Sol m-methoxy-n-pentyne then what is m n 3 4-Methoxy-2-pentyne so m 4 2 n 2 3. mong the following the number of compounds which are more acidic than phenol: (a) (b) (c) (d) 3 (e) 3 (f) (g) (h) (i) Sol gp exert electron donating effect at all positions hence decreases the acidic nature present at o/m/p increases the acidic nature (strong-i).,, when present at meta position it increases the acidic nature due to I character (1) (3) is more acidic due to more stable conjugate base i.e Dr. Sangeeta Khanna.D 11 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

12 4. ow many of the following can give Iodoform test with Na + I 2 3 (a) 3 ; (b) 3 3 ; (c) ; (d) ; 3 (e) 3 N 2 ; (f) 3 3; (g) 3 ; (h) 3 2 ; (i) 3 Sol. 5 a, b, g, h, i () alcohol with 3 3 gp; (B) methyl ketone (c) ethyl ester Na 2 5 Na Iodoform 5. ow many total products are formed in Reaction of ethanal with glycerine Sol I 2 3 cis/trans 2 (cis-d,) Trans-d, 6. n unknown organic compound () having M.F reacts with an excess of acetyl chloride gives an acetyl derivative with M.Wt Then how many hydroxyl groups are in. Sol. 3 differencein molecular w eight No. of groups = Dr. Sangeeta Khanna.D 12 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

13 Extra Questions (LL, PENL & ETER) 7. 2S 4 () (Major) Major product is Sol. ring fusion 8. fter completion of the reactions (I and II), the organic compound(s) in the reaction mixtures is(are) Reaction I: 3 3 (1.0 mol) 2 (1.0 mol) aqueous/na Reaction II: 3 3 (1.0 mol) 2 (1.0 mol) aqueous/na 3 P 2 3 Q 3 3 R 3 2 S 2 3 T Na 3 U a. Reaction I : P and Reaction II : P b. Reaction I : U, acetone and Reaction II: Q, acetone c. Reaction I : T, U, acetone and Reaction II : P d. Reaction I : R, acetone and Reaction II : S, acetone (a) If both assertion and reason are true and reason is the correct explanation of assertion. (b) If both assertion and reason are true and reason is not correct explanation of assertion (c) If assertion is correct but reason is incorrect (d) If assertion is incorrect but reason is correct 8. Statement 1: Extent of enolization decreases in a polar hydroxylytic solvent. Statement 2: If the solvent used makes hydrogen bonding with carbonyl group, it decreases the enol content. Dr. Sangeeta Khanna.D 13 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

14 a. () b. (B) c. () d. (D) 9. ssertion: Benzenediazonium chloride on boiling with water gives phenol. Reason: It is a nucleophilic substitution reaction, diazonium group is replaced by group. a. (a) b. (b) c. (c) d. (d) 10. ssertion: lthough phenoxide ion has more number of resonating structures than benzoate ion, benzoic acid is a stronger acid than phenol. Reason: Benzoic acid has larger K a value than phenol due to more stable resonating structure of benzoate ion. a. (a) b. (b) c. (c) d. (d) Sol. Both assertion and reason are correct but reason is not true explanation of assertion. The correct reason is that phenoxide ion is less stable than carboxylate ion as negative charge is delocalized only on one oxygen in phenoxide ion and on two oxygen in carboxylate ion. 6. lcohol ( ) is converted to mixture of alkene B and on heating with conc. 3 P 4. atalytic hydrogenation of B and yields the same product. ssuming that dehydration of alcohol proceed without rearrangement. lkene B on ozonolysis form cyclopentanone. Identify the correct options. is B is is is,b,d Dr. Sangeeta Khanna.D 14 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

15 7. ow many alcohol of formula 5 12 will change colour of acidic dichromate solution (only structural isomer) Sol. 7 ll Pri. & sec. alcohol i.e. 1-pentanol; 2-pentenol, 3-pentanol, 3-methyl-1-butanol, 2-methyl1-butanol; neopentylalcohol, 3-methylbutan-2-ol. 8. onsider the following reactions. In how many reactions benzene is formed as a product? 2 + a. Product b. Product c. + + Product d. Product e. Zn alc.k(excess) Product 3 Na (a) f. g. (1) r 2 3, (2) Na (a) Sol. 4 a, b, c, d ; Na (a) 9. Total number of stable isomers of molecular formula [only alcohol & ether] Sol. 7 lcohols Ethers (i) (i) (ii) 3 2 ( ) (-) (ii) 3 3 ( ) ( ) Gemdiols are not stable (iii) Dr. Sangeeta Khanna.D 15 EMISTRY ING IRLE D:\Important Data\2017\+2\rganic\Grand Test\+2 Grand Test-VI\+2 Grand Test-VI L-2.docx

Alcohol, Phenol & Ethers Carbonyl Compounds

Alcohol, Phenol & Ethers Carbonyl Compounds lcohol, Phenol & Ethers arbonyl ompounds r. Sangeeta Khanna Ph. 1 EMISTRY ING IRLE :\Important ata\017\+\rganic\grand Test\+ Grand Test-VI\+ Grand Test-VI L-1.docx r. Sangeeta Khanna Ph. Test ate: 16.9.017