Dr. Sangeeta Khanna Ph.D 1 CHEMISTRY COACHING CIRCLE D:\Important Data\2017\+2\Organic\Grand Test\+2 Grand Test - VII\+2 Grand Test-VII L-2.

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1 1 EMISTRY IG IRLE

2 Test ate: (Level 2) Topic: xygen ontaining rganic ompound RE ISTRUTIS REFULLY 1. The test is of 1 hour duration. 2. The maximum marks are This test consists of 48 questions. 4. Keep your mobiles switched off during Test in the alls. Section (Single orrect hoice Type) egative Marking [-1] This Section contains 14 multiple choice questions. Each question has four choices ), ), ) and ) out of which LY E is correct = 70 Marks 1. Reaction of with 2 S 4 dil./gs 4 Gives a compound (), which can also be obtained from a reaction of enzene with acid chloride in the presence of anhydrous ll. The compound () when treated with iodine in aq. K, yields and a yellow compound ().,, are respectively a. 6 5, 6 5, 6 6 b. 65, 6 5, 6 5 K c. 6 5,. 65, I d. 6 6, 65, I Sol. Formation of () from benzene and acid chloride in the presence of anhydrous ll indicates that it is a ketone. Formation of yellow compound () by reaction of with I 2 /K (Iodoform test) indicates that is a methyl ketone. ence is 65. Reaction of with 2 S 4 dil./gs 4 to give ketone indicates that must be () dil. 2S 4 gs l nhyd. ll 6 5 () I 2/K 6 5K + I () () 2. bserve the following reactions I) I X(lcohol) + Y (lkyl halide) II) I W + S r. Sangeeta Khanna Ph 2 EMISTRY IG IRLE

3 Sol. III) X (R 1 ) (R 2 ) (S) IV) Y (W) The reagents R 1 and R 2 can be respectively. a. ai/cetone, aq. g b. aqueous K, I c. aq. g, ai/cetone d. I, aqueous K X = Y = 2 I S =. What is the product of the following reaction? I W = 2 r(excess) K, a. b. c. d. r Sol. 4. n optically active alcohol (P) 6 10 upon catalytic hydrogenation absorbs two moles of hydrogen per mole of (P) and gives a product (Q). The compound (Q) is optically inactive and resistance to oxidation by r. Structures of (P) and (Q) respectively are 2 a., b., c., 25 d. 25, 2 2 () r 2 () () 5. (2) (1) 2 2 (4) r. Sangeeta Khanna Ph EMISTRY IG IRLE

4 rrange the hydrogens in the decreasing order of acidity. a. 1 > 2 > > 4 b. 4 > > 2 > 1 c. 2 > > 1 > 4 d. 2 > > 4 > 1 6. Which is the major product of the following reaction? + 2 product a. b. c. 2 2 d. 2 2 (i) Li (excess) 7. In the given reaction: [X] (ii) [X] is: a. Li b. c. d. Sol. cid reacts with excess of alkyl lithium to give ketone Li Li Li 4 Li Li 2Li 8. In the given reaction, the product is: 2 a. b. 2 c. d. = r. Sangeeta Khanna Ph 4 EMISTRY IG IRLE

5 Sol. 2 2 ehaves as 1, 7-dicarboxylic acid = Which pair of reactants compounds may be used to make given acetal? Sol. a. b. c. d n organic compound of molecular formula gives the following properties. (i) It evolves effervescence with a solution (ii) Its sodium salt when fused with soda lime gives neobutane. (iii) Its calcium salt when distilled gives di-ter-butyl ketone. The structure of the original compound is a. ( ) b c. 2 d. a Sol. ter bu tan oic acid Soda lime neobu tan e (i) a() 2 (ii) distil di tert butyl ketone Since the compound liberates 2 with a solution, it is an acid. It forms only one monochloro product, shows that it contains only one type of alkyl group and it may be ( ). This is proved by its conversion to neobutane and di-ter-butyl ketone. In each of the following questions three statements are given. Mark the correct answer as per following instructions (a) ll are correct (b) If all are wrong (c) If II and III is correct (d) If I and II are correct r. Sangeeta Khanna Ph 5 EMISTRY IG IRLE

6 11. I. ydrolysis of methylisocyanide produces formic acid. II. xidation of benzyl chloride with Pb( ) 2 produces benzaldehyde III. ydrogenation of enzoyl chloride in the presence of Pd-aS 4 produces benzaldehyde. a. (a) b. (b) c. (c) d. (d) 12. I. cetone gives tertiary butyl alcohol on reduction. II. cetone gives acetic acid on drastic oxidation. III. cetone undergoes bimolecular reduction with Mg g/ 2. a. (a) b. (b) c. (c) d. (d) 1. I. is imide form of urea. 2 II. onc. 2 S 4 and formic acid react to form carbon monoxides gas III. pka of chloroacetic acid is higher than that of benzoic acid. a. (a) b. (b) c. (c) d. (d) 14. I. Tartaric acid does not contain group at all II. rotonic acid does not decolourise bromine dissolved in S 2. III. lkane with same number of atoms cannot be produced from carboxylic acid. a. (a) b. (b) c. (c) d. (d) SETI (SSERTI & RES) This Section contains 10 multiple choice questions. Each question has four choices ), ), ) and ) out of which LY E is correct. (10 5 = 50 Marks) (a) Mark if both and R are correct and R is the correct reason of. (b) Mark if both and R are correct and R is not the correct reason of. (c) Mark if is correct and R is wrong. (d) Mark if is wrong and R is correct. 1. ssertion : oiling points of esters are higher than corresponding isomeric carboxylic acid. Reason : cid molecule dimerise in non aqueous solutions. a. () b. () c. () d. () 2. ssertion: Relative reactivity of acid derivatives to nucleophilic acyl substitution is : acid chloride > anhydride > amide > ester Reason: Weaker the conjugate base, better the leaving group, more the reactive it is. a. () b. () c. () d. (). ssertion: Iodoform is obtained by the reaction of acetone with hypoiodite and not with iodide. Reason: I is an oxidizing agent as well as an iodinating agent. a. () b. () c. () d. () 4. Statement 1: yclopentane-1,2-dione has more stable keto form than butane-2,-dione. Statement 2: In butane-2,-dione keto form have two keto groups at anti position a. () b. () c. () d. () r. Sangeeta Khanna Ph 6 EMISTRY IG IRLE

7 5. ssertion: iisopropyl ketone is more reactive than acetone. Reason: cidic medium makes the carbonyl group more susceptible to nucleophilic attack. a. () b. () c. () d. () u R R \ Θ R \ u \ Sol. R / R / R / 6. ssertion: ydroxy ketones are not directly used in Grignard reaction.] Reason: Grignard reagents react with hydroxyl group. a. () b. () c. () d. () 7. ssertion: Fumaric acid and maleic acid both have two groups, one \ / / \ yet their acidic strength is different. Reason: Maleic acid after the loss of + is stabilized due to intramolecular -bonding, so ease of release of + is easier in maleic acid as compare to fumaric acid. a. () b. () c. () d. () 8. ssertion: -keto butyric acid is esterified faster than butyric acid. Reason: Groups increasing the intensity of +ve charge on acidic -atom to increase the reactivity \ towards esterification / group being e withdrawing increases +ve charge so esterified faster than butyric acid. a. () b. () c. () d. () 9. ssertion: Group like 2,, attached at - atom to group makes decarboxylation faster. Reason: Strong e withdrawing group at - -atom facilitates the decarboxylation due to stable carbocation. a. () b. () c. () d. () 10. ssertion : m itrobenzoic acid is less stronger acid as compared to p nitrobenzoic acid. Reason : cetic acid is stronger acid than benzoic acid but formic acid is still stronger than both. a. () b. () c. () d. () SETI (Paragraph Type) This Section contains 2 paragraph. Each of these questions has four choices ), ), ) and ) out of which LY E is correct. 6 5 = 0 Marks Passage 1 ldehydes and ketones have sp 2 hybridised carbon and they undergo nucleophilic addition reactions. ldehydes are more reactive than ketones. ldehydes and ketones having at least one -hydrogen undergo aldol condensation, while aldehydes with no -hydrogen undergo annizzaro reaction. Ketones do not undergo annizzaro reaction r. Sangeeta Khanna Ph 7 EMISTRY IG IRLE

8 1. The products of the action of concentrated alkali on a mixture of formaldehyde and benzaldehyde are a. sodium benzoate, methanol b. benzylalcohol, sodium fomate c. sodium benzoate, sodium formate d. benzylalcohol, methanol 2 2. The product of reaction between benzaldehyde and malonic ester / 2\ 2 pyridine followed by acid hydrolysis and heating is 5 a. 6 5 () 2 b. 6 5 = c d. 6 5 = 6 5. The product/s of reaction in alkaline medium between acetophenone and benzaldehyde is/are a. 6 5 and 6 5 b. 6 5 = 6 5 c d and in presence of Passage -2 Two aliphatic aldehydes P and Q react in the presence of aqueous K 2 to give compound R, which upon treatment with provides compounds S. n acidification and heating, S gives the product shown below: 4. The compounds P and Q respectively are a. b. and and 2 and c. d. 2 and 5. The compound R is a. b. 2 r. Sangeeta Khanna Ph 8 EMISTRY IG IRLE

9 c. d The compound S is a. b. 2 2 Sol. c. d (S) + aq.k 2 (P) (Q) (R) r. Sangeeta Khanna Ph 9 EMISTRY IG IRLE

10 SETI (More than ne nswer Type) o egative Marking This Section contains 5 multiple choice questions. Each question has four choices ), ), ) and ) out of which ne or More than one answer may be correct. 8 5 = 40 Marks 1. The ether, when treated with I produces a. b. c. d. 2I 2 I, 2. Which of the following undergo decarboxylation upon heating? () () () () a. b. c. d.,. Which of the following process is involved in Reimer Tiemann s reaction a. ucleophilic substitution b. arbene intermediate c. Rearrangement d. Electrophilic substitution,,, 4. Formic acid and acetic acid can be distinguished by the action of a. conc. 2 S 4 b. Tollen s reagent c. Fehling s solution d. a,, Sol. oth give 2 with a Formic acid cetic acid onc. 2 S 4 conc S 4 o effect Tollen s Reagent + g 2 2 g lack ppt. o effect + 2u u Fehling s solution o effect Redppt. 5. Which of the following does form a stable hydrate by the addition of 2? a. Ph Ph b. c. d.,, r. Sangeeta Khanna Ph 10 EMISTRY IG IRLE

11 6. Which of the following can be the product of following reaction 2 a. b. c. d.,, Sol. 2 Ketoform enolic form Ketoform 7. Lil 4 (X) a 4 (Y) a. (X) is b. (Y) is 2 2 c.(x) is, d. (Y) is r. Sangeeta Khanna Ph 11 EMISTRY IG IRLE

12 8. Which of the following reagent(s) can be used to convert amide into a primary amine with one carbon atom less than amide? a. r 2 + a b. ar c. P 2 5 d. r 2 + a 2,, SETI E (Matrix Type) o egative Marking This Section contains 2 question. Each question has four choices (,, and ) 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 2 = 16 Marks 1. Match each of the compounds in olumn I with its characteristic reaction(s) in olumn II. (ne or More than ne Match) olumn I olumn II (a) 2 2 (p) Reduction with Pd-/ 2 (b) 2 (q) Reduction with Snl 2 /l (c) = 2 (r) evelopment of foul smell on treatment with chloroform and alcoholic K (d) (s) Reduction with diisobutyl aluminium hydride (IL-) (t) lkaline hydrolysis Sol. p, q, s, t; s, t ; p; r 2. Match compounds in olumn I with their characteristic test(s)/reaction(s) given in olumn II. (ne or More than ne Match). olumn I olumn II () Θ (p) ompound give effervescence with a 2 l () I (q) gives positive Fel test () (r) gives white precipitate with g l () (s) reacts with aldehydes to form the corresponding 2 r hydrazone derivative 2 Sol. r, s ; p, q ; q, r ; s SETI F (Integer Type) o egative Marking This Section contains 8 questions. The answer to each question is a single digit integer ranging from 0 to 9. (8 5 = 40 Marks) 1. Mgr (i)2 2 5 n 2n1. The value of n is (ii)2 Sol. 2 l + a 2. The number of moles of ethanoyl chloride which produces 10.2 g of ethanoic anhydrie on reaction with sodium acetate is 10 -x, X is: Sol. 1. ow many different Grignard reagents having single romine can give n-butane as product (excluding stereisomer), when react with 2 5 Sol Mgr, 2 Mgr bove Grignard reagent when reacts with ethanol, normal butane as a product. 4. ow many isomeric ketones can be formulated by 6 12? r. Sangeeta Khanna Ph 12 EMISTRY IG IRLE

13 Sol. 7 ; ; ; ; \ / d/ x MgI + ( ) 2 ( ) 2 ; imethyl phthalate umber of moles (x) of Grignard reagent consumed in the above reaction is: Sol n organic compound having molecular formula on acetylation forms a compound having molecular weight 4. umber of hydroxy groups (-) in compound is: Sol. 4 n acetylation, group get changed into means per group molecular weight increases by 42. Molecular wt. of Molecular wt. after acetylation = 4 increases in molecular wt. = = umber of groups = omplete the following reactions and find out number of oxygen atom present in compound () i) + a () gs 4 2S 4 () () /Zn () Sol. = = = = 8. n organic compound on treatment with ethyl alcohol gives a carboxylic acid and compound. ydrolysis of under acidic conditions gives and. xidation of with KMn 4 also gives. on heating with a() 2 gives E. E does not give Tollen s test and does not reduce Fehling s solution but form a 2,4-dinitrophenyl hydrazone. ow many carbon are present in product (E). Sol. = = a() 2 ( ) 2 a = 5 2 E = + a r. Sangeeta Khanna Ph 1 EMISTRY IG IRLE = 5 2 Ester