NURTURE COURSE ACIDIC STRENGTH & BASIC STRENGTH Acidic Strength & Basic Strength ALLEN ACIDIC STRENGTH & BASIC STRENGTH EXERCISE # I 1. Write correct order of acidic strength of following compounds : O O || || (i) (a) NO 2 - CH 2 - C - O - H (b) F - CH 2 - C - O - H O O || || (c) Ph - CH 2 - C - O - H (d) CH 3 - CH 2 - C - O - H O O || || (ii) (a) CH 3 - CH 2 - CH - C - O - H (b) CH 3 - CH - CH 2 - C - O - H | | F F O || (c) CH 2 - CH 2 - CH 2 - C - O - H | F O || (iii) (a) Cl - CH 2 - C - O - H O || (b) Cl - CH - C - O - H | Cl Cl O | || (c) Cl - C - C - O - H | Cl (b) CH 3 - CH - O - H | CH 3 (iv) (a) CH3–CH2–O–H CH3 (c) CH3–C–O–H CH3 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (v) (a) E COOH (b) COOH (c) COOH COOH (vi) (a) | COOH (b) CH2 (vii) (a) H–F (b) H–Cl (c) H–Br (d) H–I (viii) (a) CH4 (b) NH3 (c) H2O (d) H–F COOH COOH (ix)(a) F–CH2–CH2–O–H (b) NO2–CH2–CH2–O–H (c) Br–CH2–CH2–O–H (x) (a) CH3COOH CH 2 - COOH (c) | CH 2 - COOH (b) CH3CH2OH Å (d) NH3 - CH2 - CH2 - O - H (c) C6H5OH (d) C6H5SO3H 1 JEE-Chemistry 2. ALLEN Explain which is a stronger acid. O || (a) CH3CH3 or BrCH2NO2 (b) CH 3 - C - CH 3 or O || CH 3 - C - CH 2CN (d) or OH or (c) O=C–CH 3 3. Which of the following would you predict to be the stronger acid ? (a) Benzoic acid or para-nitrobenzoic acid (b) CH3–CH2–CH2–OH or CH3–CH = CH – OH (c) CH3 – CH = CH – CH2 – OH or CH3 – CH = CH – OH 4. Arrange the given phenol & its derivative in their decreasing order of acidity : (I) C6H5–OH (II) F OH (III) Cl OH (IV) O2N OH Select the correct answer from the given code: (A) IV > III > I > II (B) 8. (C) (D) CH2=CH–CH3 (C) (D) Which of the following is weakest acid? (A) 7. (D) IV > I > III > II Which one of the following is the most acidic? (A) 6. (C) IV > III > II > I (B) Arrange pH of the given compounds in decreasing order: (1) Phenol (2) Ethyl alcohol (3) Formic acid (4) Benzoic acid (A) 1 > 2 > 3 > 4 (B) 2 > 1 > 4 > 3 (C) 3 > 2 > 4 > 1 (D) 4 > 3 > 1 > 2 Arrange acidity of given compounds in decreasing order: (I) CH3–NH–CH2–CH2–OH (II) CH3–NH–CH2–CH2–CH2–OH Å (III) (CH 3 )3 N - CH 2 - CH 2 - OH (A) III > I > II 2 (B) III > II > I (C) I > II > III (D) II > I > III node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 5. (B) IV > II > III > I E Acidic Strength & Basic Strength ALLEN 9. Consider the following compound O || CH 3CCOOH I II III Which of the above compounds reacts with NaHCO3 giving CO2 (A) I, II and III 10. (B) I and III (C) II and III Say which pka belong to which functional group in case of following amino acids : (i) cysteine : 1.8, 8.3 & 10.8 (ii) glutamic acid : 11. (D) I and II : 2.19, 4.25, 9.67 Record the following sets of compounds according to increasing pKa ( = – log Ka) (a) , , cyclohexane carboxylic acid. (b) 1-butyne, 1-butene, butane (c) Propanoic acid, 3-bromopropanoic acid, 2-nitropropanoic acid (d) Phenol,o-nitrophenol, o-cresol (e) Hexylamine, aniline, methylamine 12. Write correct order of acidic strength of following compounds: O–H NO2 (b) (i) (a) NO2 (c) node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 E O–H O–H (ii) (a) NO2 NO2 (c) Cl O–H N O CH3 O–H O–H O NO2 O–H (b) NO2 (iii)(a) (d) NO2 NO2 \ O–H O–H O–H (b) N O O (c) O–H (d) O N O 3 JEE-Chemistry ALLEN O–H O–H O–H (iv) (a) (b) Cl (v) (a) (c) (d) O–H O–H O–H O–H (b) (c) Cl Cl O C–O–H O C–O–H (vi)(a) O C–O–H (vii) CH3 (b) (a) O C–O–H (b) (c) NO2 N O O Select the strongest acid in each of the following sets : OH OH (b) (i) (a) OH OH (c) (d) CH3 NO2 Cl NH2 OH OH OH OH (ii) (a) (b) (c) NO2 OH (d) CH3 F OH OMe (iii)(a) OH OH (b) (c) (d) OMe OMe OH OH (iv)(a) (b) NO2 4 NO2 OH NO2 (c) NO2 OH NO2 (d) NO2 NO2 NO2 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 13. O C–O–H NO2 E Acidic Strength & Basic Strength ALLEN 14. 15. 16. The strongest acid is : (A)HF (B) CH3CO2H (C) HF + SbF5 The weakest acid (does not show acidic character) is : (A)HC º CH (B) CH2 = CH2 (C) Me3CH Which of the following is most acidic : (A) (B) (D) Ph3CH COOH COOH COOH (D) H2S (C) COOH (D) CH3 NO2 17. CH3 Paragraph for Question 17 to 18 The most important condition for resonance to occur is that the involved atoms in resonating structure must be coplanar or nearly coplanar for maximum delocalisation. If this condition does not fulfil, involved orbitals cannot be parallel to each other and as a consequence delocalisation cannot occcur. Bulky groups present on adjacent atoms inhibit the planarity of atoms involved in resonance. This phenomenon is known as steric inhibition of resonance. Steric inhibition of resonance has profound effect on (1) Physical properties (2) Acidity and basicity (3) Reactivity of organic compounds Arrange the following in the decreasing order of basicity : CH3–N– CH3 NH2 (I) (II) NH2 NH2 (III) (IV) NO2 NO2 18. (A) I > II > III > IV (B) IV > III > II > I (C) II > I > IV > III (D) I > IV > III > II Which of the following is most acidic : (B) (A) COOH COOH COOH (C) COOH (D) CH3 CH3 19. How many following compounds are more acidic than water ? node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (a) E CH3 SO3H (b) HCl (c) CH3 – C º CH (d) (g) (h) CO 2H OH (e) (f) OH NO2 (i) NaOH 20. Select correct order regarding acidic strength of given compounds : (1) o-methylbenzoic acid (2) m-methylbenzoic acid (3) p-methylbenzoic acid (4) benzoic acid (A)1 > 2 > 3 > 4 (B) 4 > 3 > 2 > 1 (C) 1 > 4 > 2 > 3 (D) 3 > 2 > 4 > 1 5 JEE-Chemistry ALLEN EXERCISE # II 1. Write decreasing order of basic strength of following : – – – (b) NH2 (i) (a) CH3 – – – (c) OH (d) F – (d) I – (ii) (a) F (b) Cl (c) Br (iii) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (iv) (a) NH3 (b) MeNH2 (c) Me2NH (d) Me3N (Gas phase) (v) (a) R–NH2 (b) Ph–NH2 (c) R - C - NH 2 || O (b) (c) (in H2O) O (vi) (a) NH NH N Me NH2 NH2 (vii)(a) (b) (c) NH N (b) O2N (c) NH2 (ix) (a) NH2 NH2 (b) Å NH3 2. F Me (c) H Write decreasing order of basic strength of following : ·· ·· (i) (a) CH3–CH2– N H 2 (b) CH3–CH= NH · · (ii) (a) CH 3 - C - NH 2 || O 6 (d) CH 3 Cl NH2 ·· ·· (c) CH3–Cº N · · (b) CH3–CH2– NH 2 (c) CH 3 - C - N H 2 || NH ·· · · · · (d) NH 2- C - N H 2 || N H ·· node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (viii) (a) N N E Acidic Strength & Basic Strength ALLEN NH2 (iii) (a) (b) (c) N H N NH2 NH2 (iv) (a) (b) (d) CN OMe NH2 NH2 NH2 (b) (c) O NH2 NO2 NO2 NO2 Me NH2 (c) NO2 (v) (a) (vi) (a) NH2 NH2 N NH2 Me (b) Me O O Me N O O node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 NH–C–CH3 E NH–CH2–CH3 NH2 (vii)(a) (b) (c) (viii) (a) (b) (c) (d) (ix) (a) (b) (c) (d) 7 JEE-Chemistry 3. ALLEN Select the strongest base in following compound : S O (i) (a) (b) N (c) (d) N N N H H H NH2 (ii) (a) (b) NH (c) (d) N N H N (iii) (a) (b) (c) N N N N H H CH3 Et Ph H Me N N N + N¯Li (iv) (a) (b) (c) (d) Arrange the following compound in decreasing order of their basicity. (i) (a) H2C = CHNa (b) CH3CH2Na NH2 (ii) (a) (c) CH3CH2ONa NH2 CH2 – NH2 (c) (b) (d) HC º CNa (d) NO2 (iii) (a) HO¯ 5. (b) NH3 C – NH2 O (c) H2O (d) HSO4¯ (C) I > II > III (D) III > I > II Correct decreasing order of basic strength - NH2 NH2 N N N H (I) NMe2 H–N N H–N (II) (III) Of following compound (A) III > II > I 8 (B) II > I > III node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 4. (d) E Acidic Strength & Basic Strength ALLEN 6. Consider the following bases: (I) o-nitroaniline (II) m-nitroaniline (III) p-nitroaniline The decreasing order of basicity is: (A) II > III > I 7. (B) II > I > III (C) I > II >III (D) I > III > II Consider the basicity of the following aromatic amines: (I) aniline (II) p-nitroaniline (III) p-methoxyaniline (IV) p-methylaniline The correct order of decreasing basicity is: (A) III > IV > I > II 8. (C) I > II > III > IV (D) IV > III > II > I Which one of the following is least basic in character? (A) 9. (B) III > IV > II > I (B) (C) (D) In each of the following pair of compounds, which is more basic in aqueous solution? Give an explanation for your choice: (a) CH3NH2 or CF3NH2 (b) CH3CONH2 or H2N NH2 (c) CH3CH2CH2NH2 or CH3CN (d) C6H5N(CH3)2 or 2,6-dimethyl-N-N-dimethylaniline 10. Choose the member of each of the following pairs of compunds that is likely to be the weaker base. (a) H2O or H3O+ (b) Cl¯, SH¯ (c) F¯, OH¯, NH¯, 2 CH¯ 3 (d) HF, H2O, NH3 (e) OH¯, SH¯, SeH¯ node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 11. E Explain which compound is the weaker base. (a) (b) CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2– or COO¯ (c) | COOH or COOH | COOH (d) or 9 JEE-Chemistry 12. ALLEN Arrange the basic strength of the following compounds. (a) OH¯ CH3COO¯ (i) Cl¯ (ii) (b) CH º C¯ (iii) CH2 = CH¯ (i) CH3CH 2¯ (ii) (iii) (c) CH2 = CHCH2NH2 CH3 CH2 CH2 NH 2 CH º C – CH2NH2 (i) (ii) (iii) (i) (ii) (iii) (d) Arrange the following compounds in order of increasing basicity. (a) CH3NH2, CH3 NH 3Å , CH3NH¯ 14. Which of the following is most basic : N N N (A) 15. N N (B) (C) N N (D) N Basicity order of N in following compound is : O CH3 H2N– C– CH 2 c Nb N CH3 d (A) b > d > a > c 10 (b) CH3O¯, CH3NH¯, CH3CH¯2 CH3 CH2 – NH – C– CH 3 NH a CH3 (B) a > b > d > c (C) a > b > c > d (D) a > c > b > d node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 13. E Acidic Strength & Basic Strength ALLEN 16. The conjugate base of serotonin (used as tranquilisers) is given as follows : O CH2–CH2–NH2 – •• N H How many basic groups present in following compound ? 17. The structure of saccharin is given as follows : O C NH [Provided N is the donor atom in all cases] S O O How many following compounds are more basic than saccharin ? O C (i) CH3– C – NH2 (ii) H2N– C – NH 2 NH CH2–NH2 (vi) O (iv) N–H C O N node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (v) NH (iii) CH3 – C – NH2 E 11 JEE-Chemistry ALLEN EXERCISE # III 1. In given reaction Gas liberated is/are O C O–H 14 NaHCO3 SO3H (B) SO3 & 14CO2 (A) CO2 & SO3 2. (D) SO2 only Arrange marked atom in decreasing order of acidic strength 2 H O 1 3 H N–H (A) 1 > 2 > 3 3. (C) 14CO2 only Column - I (B) 3 > 2 > 1 (C) 2 > 1 > 3 (D) 2 > 3 > 1 Column-I OH (A) (P) React with NaOH OH (B) (Q) React with NaHCO3 OH (C) (R) React with NaH OH NO2 (D) (S) React with Na NO2 (T) React with NaNH2 12 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 NO2 E Acidic Strength & Basic Strength ALLEN 4. Compound which can give effevescences with NaHCO3 OH COOH (i) O (Salicylic acid) OH (ii) (Squaric acid) O SO3H (iii) OH OH O2N (Benzene sulphonic acid) NO2 (iv) (Picric acid) NO2 OH (v) Ph–CH=CH–COOH (cinnamic acid) (vi) OH CH2–OH OH (vii) (viii) OH NO2 (ix) (x) NO2 5. NO2 Statement-1 : For the given two compounds-I is more acidic than compounds-II. H3C NO2 CH3 H3C CN CH3 OH (II) OH (I) and Statement-2 : Due to presence of –CH3 group at ortho positions to –NO2 ; the plane of –NO2 deviates, w.r.t plane of ring. (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 correct explanation for Statement-1. (C) Statement-1 is True, Statement-2 is False. node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (D) Statement-1 is False, Statement-2 is True. E 6. Statement 1 : O N (I) O is more basic than N H (II) O and Statement 2 : Lone pair electrons on nitrogen in compound (I) does not participate in resonance. (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 correct explanation for Statement-1. (C) Statement-1 is True, Statement-2 is False. (D) Statement-1 is False, Statement-2 is True. 13 JEE-Chemistry 7. ALLEN Match Column-I with Column-II. Column - I (Facts) (A) Guanidine H2N–C–NH2 is example Column - II (Reasons) (P) Resonance stabilisation of conjugate acid of strong base NH of strong base. (B) Carbanion stability CCl3 > CF3 (Q) Due to s-character of central atoms (C) Alkyne is more acidic than alkene (R) Due to d-orbital resonance (D) Acidity : (S) Due to formation of aromatic anion < (T) Stability of conjugate base due to more number of identical resonating structure 8. Match Column-I with Column-II. Column - I (Compounds) Column - II (pKa) (A) HO F (P) 7.15 (B) HO Cl (Q) 10.14 (C) HO NO2 (R) 9.98 (D) HO CH3 (S) 9.38 (T) pKa is more than phenol (Comprehension) (Q.9 to Q.11) Observe the following feasible reactions : (i) ONa COONa + OH + NO 2 OH NO 2 ONa NO2 + NaHCO3 ¾® (ii) NO 2 14 + H2CO3 NO 2 ONa (iii) NO2 OH + H2CO3 ¾® + NaHCO3 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 COOH E Acidic Strength & Basic Strength ALLEN Answer the following question : 9. Which of the following is the correct order of acidic strength. OH COOH (A) OH NO2 > > H2CO3 > OH COOH (B) > NO 2 > > H2CO3 NO 2 OH COOH (C) OH NO2 OH NO2 > H2CO3 > > (D) None NO 2 10. Which of the following compound does not react with NaHCO3 OH OH (B) (A) (C) COONa + NaHCO3 ¾® (A) NH2 NHNa OH (C) + H2O + CO2 ONa + NaHCO3 ¾® COONa (D) + H2O + CO2 + NaHCO3 ¾® (B) node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 NO2 Identify the feasible reactions COOH E COOH (D) NO 2 NO2 CH3 11. OH ¾® NO2 COO¯ COOH COOH + + H2O + CO2 + NO2 15 JEE-Chemistry 12. ALLEN Identify the non-feasible reaction •• CH3—C º C + NH3 (A) CH3–C º CH + NH2¯ CH3CH2ONa + H2 (B) CH3CH2—OH + NaH CH3ONa + H2O (C) CH3—OH + NaOH HCºCNa + H2O (D) HCºCH + NaOH 13. Select the number of compounds in which deprotonation gives aromatic anion : O (A) HN NH HO–CH2 O H (B) HO O O Barbituric acid O O O (C) (D) N | H OH HO Ascorbic acid (Vitamin-C) O Paragraph for Questions 14 and 15 Aqueous Layer Organic Layer OH Aqueous NaHCO3 COOH Organic Layer Aqueous Layer Identify salt 'A' ? – + (A) + COO Na (B) + – Na (C) (D) All of these Identify compound 'C' ? (A) OH COOH OH (B) (C) (D) COOH 16 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 – O Na 15. (Compound - C) (Salt - A) Mixture of 3-compounds in hexane 14. (Salt - B) Aqueous NaOH E Acidic Strength & Basic Strength ALLEN EXERCISE # IV (JEE-MAIN) 1. [AIEEE-2002] Picric acid is COOH (1) OH COOH (2) NO 2 (3) NO2 COOH NO2 (4) NH 2 OH NO2 2. (1) NH3 3. [AIEEE-2002] Which of the following speices acts both as bronsted acid & base – (2) OH¯ (3) HSO Q4 (4) 1 and 3 both The correct order of increasing basic nature for the bases NH3, CH2NH2 and (CH3)2NH is[AIEEE-2003] 4. (1) CH3NH2 < NH3 < (CH3)2NH (2) (CH3)2NH < NH3 < CH3NH2 (3) NH3 < CH3NH2 < (CH3)2NH (4) CH3NH2 < (CH3)2NH < NH [AIEEE-2004] Consider the acidity of the carboxylic acids(i) PhCOOH (ii) o–NO2C6H4COOH (iii) p-NO2C6H4COOH (iv) m-NO2C6H4COOH which of the following is the correct order of acidity- 5. (1) i > ii > iii > iv (2) ii > iv > iii > i (3) ii > iv > i > iii (4) ii > iii > iv > i [AIEEE-2004] Which of the following is the strongest base (1) NH2 (2) NHCH3 (3) NH2 (4) CH2NH2 CH3 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 6. E 7. 8. (1) CH3CH2COOH (2) (CH3)2CHCOOH (3) HCOOH (4) CH3COOH [AIEEE-2005] Amongest the following the most basic compound is(1) p-nitro aniline (2) Acetanilide (3) Aniline (4) Benzylamine [AIEEE-2005] What is the conjugate base of OH¯? (1) H2O 9. [AIEEE-2005] Among the following acids which has the lowest pk a value- (2) O2 (3) O2– Among the following acids which has the lowest pKa value? (1) HCOOH (2) CH3COOH (3) CH3CH2COOH (4) (CH3)2CH–COOH (4) O¯ [AIEEE-2005] 17 JEE-Chemistry 11. 12. 13. 14. [AIEEE-2006] The correct order of increasing acid strength of the compounds is (a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) (1) d < a < c < b (2) d < a < b < c (3) a < d < c < b (4) b < d < a < c Me Me CO2 H [AIEEE-2007] Which one of the following is the strongest base in aqueous solution ? (1) Trimethylamine (2) Aniline (3) Dimethylamine (4) Methylamine The correct order of increasing basicity of the given conjugate base (R=CH3) is :- [AIEEE-2010] (1) RCOO < HC º C < NH 2 < R (2) RCOO < HC º C < R < NH 2 (3) R < HC º C < RCOO < NH 2 (4) RCOO < NH 2 < HC º C < R [AIEEE-2011] The strongest acid amongst the following compounds is ? (1) CH3CH2CH(Cl)CO2H (2) ClCH2CH2CH2COOH (3) CH3COOH (4) HCOOH The correct order of acid strength of the following compounds :A. Phenol B. p-Cresol C. m-Nitrophenol D. p- Nitrophenol [AIEEE-2011] is :- 15. (1) C > B > A > D (2) D > C > A > B (3) B > D > A > C (4) A > B > D > C [JEE(Main)-2012] In the following compounds : (I) N H (II) N (III) O N (IV) H N H the order of basicity is as follows : 16. 17. 18 (1) IV > III > II > I (2) II > III > I > IV (3) I > III > II > IV (4) III > I > II > IV The most basic compound among the following is :(1) Acetanilide (2) Benzylamine (3) p-Nitro aniline (4) Aniline The order of basicity of amines in gaseous state is :(1) 3° > 2° > NH3 > 1° (2) 1° > 2° > 3° > NH3 (3) NH3 > 1° > 2°> 3° (4) 3° > 2° > 1° > NH3 [JEE(Main)-2012] [JEE(Main)-2013] node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 10. ALLEN E Acidic Strength & Basic Strength ALLEN 18. OH OH ; Cl (I) 19. OH ; OH ; CH3 (II) NO2 (III) OCH3 (IV) (1) II > IV > I > III (2) I > II > III > IV (3) III > I > II > IV (4) IV > III > I > II [JEE(Main)-2014] The conjugate base of hydrazoic acid is :(1) HN3¯ 20. [JEE(Main)-2013] Arrange the following compounds in order of decreasing acidity : (2) N¯3 (3) N¯2 (4) N–3 Which one of the following compounds will not be soluble in sodium bicarbonate ? [JEE(Main)-2014] 21. (1) Benzene sulphonic acid (2) Benzoic acid (3) o-Nitrophenol (4) 2, 4, 6 - Trinitrophenol Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value ? [JEE(Main)-2014] (1) (CH3)3N 22. 23. node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 E (3) (CH3)2NH (4) CH3NH2 Among the following oxoacids, the correct decreasing order of acid strength is : [JEE(Main)-2014] (1) HClO4 > HClO3 > HClO2 > HOCl (2) HClO2 > HClO4 > HClO3 > HOCl (3) HOCl > HClO2 > HClO3 > HClO4 (4) HClO4 > HOCl > HClO2 > HClO3 Among the following compounds, the increasing order of their basic strength is:(I) 24. (2) C6H5NH2 (II) (III) (1) (II) < (I) < (III) < (IV) (2) (I) < (II) < (IV) < (III) (3) (II) < (I) < (IV) < (III) (4) (I) < (II) < (III) < (IV) (IV) [JEE(Main)-On-Line 2017] [JEE(Main)-2018] The increasing order of basicity of the following compounds is : (a) (b) (1) (b) < (a) < (c) < (d) (3) (d) < (b) < (a) < (c) (c) (d) (2) (b) < (a) < (d) < (c) (4) (a) < (b) < (c) < (d) 19 JEE-Chemistry ALLEN EXERCISE # V (J-ADVANCED) OH OH I CH3 II OH OH NO2 2. 3. 4. NH2 (CH3)2NH CH3CH2NH2 , (A) 2 > 1 > 3 > 4 20 NO 2 IV O NH 1 6. III The order of acidity is (A) III>IV>I>II (B) I>IV>III>II (C) II>I>III>IV (D) IV>III>I>II Although phenoxide ion has more number of resonating structures than benzoate ion, benzoic acid is a stronger acid than phenol. Why ? [IIT-JEE-1997] Amongst the following, the most basic compound is [IIT-JEE-2000] (A) C6H5NH2 (B) p–NO2–C6H4NH2 (C) m–NO2–C6H4NH2 (D) C6H5CH2NH2 The correct order of basicities of the following compounds is : [IIT-JEE-2001] CH3–C 5. [IIT-JEE-1996] In the following compounds 2 , 3 CH3CNH 2 , 4 (B) 1 > 3 > 2 > 4 (C) 3 > 1 > 2 > 4 (D) 1 > 2 > 3 > 4 Statement-I : p-Hydroxybenzoic acid has a lower boiling point that o-hydroxybenzoic acid. Because Statement-II : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [IIT-JEE-2003] (A) Statement-I is True, Statement-II is True ; Statement-II is a correct explanation for Statement-I (B) Statement-I is True, Statement-II is True; Statement-II is NOT a correct explanation for Statement-I (C) Statement-I is True, Statement-II is False. (D) Statement-I is False, Statement-II is True. Match Ka values with suitable acid : [IIT-JEE-2003] Ka Acid (A) 3.3 × 10–5 (p) (B) 4.2 × 10–5 (q) Me— —COOH (C) 6.3 × 10–5 (r) —COOH (D) 6.4 × 10–5 (s) MeO— —COOH (E) 30.6 × 10–5 (t) —COOH —COOH Cl— O2N— node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 1. E Acidic Strength & Basic Strength ALLEN 7. [IIT-JEE-2004] (a) Which of the following is more acidic and why ? Å Å NH3 NH3 (I) F (II) HOOC OH 8. 2Moles NaNH 2® ¾¾¾¾¾¾¾ A. The product (A) will be : O2N [IIT-JEE-2007] CH OH HOOC 1 O1 OOC OH (B) O2N (A) O2N CH C1 O1 1 OH HOOC OOC OH OH (D) O2N (C) O2N C1 CH O1 O1 node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 9. E 10. [IIT-JEE-2009] The correct acidity order of the following is : OH OH (I) (II) Cl COOH COOH (III) (IV) CH3 (A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II) (C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I) Amongst the following, the total number of compounds soluble in aquesous NaOH is: [IIT-JEE-2010] CH3 H3 C OCH2CH3 COOH NO2 OH N CH2OH OH CH2CH3 CH2CH3 COOH N H3 C CH3 21 JEE-Chemistry 11. 12. ALLEN (A) p-nitrophenol (B) p-hydroxybenzoic acid (C) o-hydroxybenzoic acid (D) p-toluic acid [IIT-JEE-2012] The carboxyl functional group (–COOH) is present in (A) picric acid 13. [IIT-JEE-2011] Among the following compounds, the most acidic is (B) barbituric acid (C) ascorbic acid (D) aspirin Identify the binary mixtures (s) that can be separated into the individual compounds, by differential [IIT-JEE-2012] extraction, as shown in the given scheme - NaOH(aq) Binary mixture containing Compund 1 and compound 2 14. NaHCO3(aq) Compound 1 + Compound 2 Compound 1 + Compound 2 (A) C6H5OH and C6H5COOH (B) C6H5COOH and C6H5CH2OH (C) C6H5CH2OH and C6H5OH (D) C6H5CH2OH and C6H5CH2COOH The compound that does NOT liberate CO2, on treatment with aqueous sodium bicarbonate solution, [JEE-ADVANCED-2013] is (A) Benzoic acid 15. (B) Benzenesulphonic acid (C) Salicylic acid (D) Carbolic acid (phenol) Hydrogen bonding plays a central role in the following phenomena [JEE-ADVANCED-2014] (A) Ice floats in water (B) Higher Lewis basicity of primary amines than tertiary amines in aqueous solutions (D) Dimerisation of acetic acid in benzene 16. [JEE-ADVANCED-2017] The order of basicity among the following compounds is NH NH2 H3C I 22 NH 2 N NH HN N NH H2N II III (A) II > I > IV > III (B) IV > II > III > I (C) I > IV > III > II (D) IV > I > II > III IV node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (C) Formic acid is more acidic than acetic acid E Acidic Strength & Basic Strength ALLEN ANSWER KEY EXERCISE # I 1. (i) a > b > c > d, (ii) a>b>c, (v) c > b > a, (vi) a > b > c (ix) d > b > a > c, (x) (iii) c > b > a, (iv) a > b > c, (vii) d > c > b > a , (viii)d > c > b > a, d > a > c> b 2. (a) 2 ; (b) 2 ; (c) 1 ; (d) 1 3. (a) 2 ; (b) 2 ; (c) 2 4. (C) 6. (B) 8. (A) (A) 10. (i) cysteine : 11. (a) 3 < 2 < 1 ; (b) 1 < 2 < 3 ; (c) 3 < 2 < 1 ; (d) 2 < 1 < 3 ; (e) 2 < 3 < 1 12. (i) 7. d > c > a > b, (v) a > b > c, (B) 9. 5. (B) (ii) glutamic acid : (ii) a > b > c, (iii) c > a > b > d, (vi) b > a (vii) c > a > b (iv) d > b > c > a, 13. (i) b , (ii) a, (iii) b , (iv) b 14. (C) 15. (C) 17. (C) 19. (4) 20 (C) 18. (B) 16. (B) EXERCISE # II 1. 2. (i) a > b> c> d, (ii) a > b > c > d, (iii) c > b> d> a , (v) a > b > c, (vi) c > b > a (vii) c > a > b, (viii) b > c > a, (ix) c > d > b > a (i) (ii) d > c > b > a, (iii) b > c > a, (iv) d > c > b > a, (vi) b > a, (vii) c > b > a, (viii) d > a > b > c a > b > c, (v) b > a > c, (iv) d > c > b > a node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 (ix) d > c > b > a E 3. (i) d, (ii) b, (iii) a, (iv) a 4. (i) b > a > d > c, 5. (A) 9. (a) i , (b) ii , (c) i , (d) ii 11. (a) 2; (b) 1;(c) 2; (d) 2 12. (a) 1 > 2 > 3 ; (b) 1 < 2 < 3 ; (c) 3 < 1 < 2 ; (d) 2 < 1 < 3 13. (a) 2 < 1 < 3 ; (b) 1 < 2 < 3 16. 3, 3 basic groups are NH 2 ; –NH–;O — (ii) b > a > c > d, (iii) a > b > c > d 6. (A) 7. (A) 8. (A) 10. (a) 2 ; (b) 1 ; (c) 1 ; (d) 1 ; (e) 3 •• 14. (C) 17. 15. (B) (6) 23 JEE-Chemistry ALLEN EXERCISE # III 1. (C) 2. (C) 3. (A) – R, S, T ; (B) – P, R, S, T ; (C) – P, Q, R, S, T ; (D) – P, Q, R, S, T 4. (i) , (ii) (iii) (iv), (v) (ix) 7. 5. (D) 6. (A) (A) – P,T ; (B) – R; (C) – Q ; (D) – S, T 8. (A) – R ; (B) – S; (C) – P ; (D) – Q, T 9. (A) 10. (A) 11. (A, D) 13. (A, B, C, D) 14. (B) 15. (C) 12. (D) EXERCISE # IV (JEE-MAIN) 1. (3) 2. (4) 3. (3) 4. (4) 5. (4) 6. (3) 7. (4) 8. (3) 9. (1) 10. (2) 11. (3) 12. (1) 13. (1) 14. (2) 15. (3) 16. (2) 17. (4) 18. (3) 19. (2) 20. (3) 21. (3) 22. (1) 23. (3) 24. (2) EXERCISE # V (J-ADVANCED) 1. (D) 2. Benzoate has equivalent resonating structures 3. (D) 4. (B) 6. A-(s) ; B-(q) ; C-(p) ; D-(r) ; E-(t) 7. (II is most acidic) 8. 11. 15. (D) (C) 9. (A) 10. (4) (C) 12. (D) 13. (B, D) 14. (D) (A, B, D) 16. (D) node06\B0AH-AI\Kota\JEE(Advanced)\Nurture\Chem\Sheet\Acidic Strength & Basic Strength\Eng.p65 5. 24 E
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