Acidicity Basicity & H- Bonding Tautomerism (Q.B.)12th

BANSALCLASSES TARGET IIT JEE 2007

ORGANIC

CHEMISTRY

XII (ALL)

QUESTION BANK ON

ACID AC IDIT ITY Y, BA BASI SICI CITY TY H--BONDING H & TAUTOMERISM

ACIDITY,, BASICITY ACIDITY BASICITY,, H-BONDING & TAUTOMERI TAUTOMERISM SM Q.1 (a) (b)) (b (c)) (c

Write equ equatio ations ns sho showing wing the Lew Lewis is acidacid-bas basee reacti reaction on that take takess place place whe when n Methyl al alcohol re reacts wi with BF BF3. Meth Me thy yl chl hlor orid idee re reac acts ts wi with th Al AlCl Cl3. Dim imeethyl eth theer re reaacts with BF3.

Q.2

Whic Wh ich h of the the foll follow owin ing g are are lewi lewiss acid acidss & whic which h are are lewi lewiss base bases? s?

⋅⋅

(a) CH3CH 2 − N − CH3 | CH3 (d)

•• — • • •• • •

CH 3 | (b) CH 3 − C ⊕ | CH 3 (e) (CH3)3B

Br

(c) (C6H5)3 P:

− (f) H :

Q.3 (a) (b) (c)

Which would Which would you you expe expect ct to be be the stron stronger ger acid acid?? Explain Explain you yourr reason reasoning ing in in each each instanc instance. e. CH2ClCO2H or CHCl2CO2H CCl3CO2H or CHCl2CO2H CH2FCO2H or CH2FCH2CO2H

Q.4

(a) (b) (c) (d) (e) (f) (g)

Write equa equation tionss for the the acid acid base base react reaction ion that that would would occu occurr when when each each of the the followin following g compou compounds nds or or solution are mixed. In each case label the stronger acid & stronger base,& the weaker acid & weaker base. NaH is added to CH3OH NaNH2is added to CH 3CH2OH Gaseous NH3 is added to ethyl lithium in hexane NH4Cl is added to NaNH 2 in liq. NH3 (CH3)3CONa is added to H 2O NaOH is added to (CH3)3 C-OH C2H5OH is added to a solution of HC ≡ C–Na+ in liquid NH3.

Q.5

CH3CH2MgBr + CH3C ≡ CH → A + B

Q.6

Choose Cho ose the the membe memberr of each each of the follow following ing pairs pairs of compun compunds ds that that is likel likely y to be be the stron stronger ger base base..

Q.7

(a) NH 2− or NH3

(b) OH– or H2O

(c) OH– or SH–

(d) CH3CH2O– or

O || (e) CH 2 − C − OH or CH3CH2O–

(f) NH3 or NH ⊕ 4

Choose the Choose the membe memberr of each each of the the followin following g pairs pairs of comp compunds unds that is likely likely to to be the weak weaker er base. base. – 2– – – ⊕ (a) H2O or H3O (b) H2S, HS , S (c) Cl , SH (d) F–, OH–, NH2–, CH3−

B ansal C lass ssees

(e) HF, H2O, NH3

(f) OH–, SH–, SeH–

Q. Ba Bank nk on Ac Acid idiity, Basi sici citty, HH-B Bond ndiing & Taut uto omer eriism

[2] [2 ]

Q.8

Label the react Label reactants ants in these these acid – base base reacti reactions ons as Lewis Lewis acids (elec (electrophi trophiles) les) or Lewis Lewis bases bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the recations.

(a)

CH3 •O•••

(b)

CH 3 − O − CH 3 | CH 3

••

—

••

•

••

••

••

••

—

•

+ CH 3 − Cl •  → → CH 3 − O − CH 3 + •• Cl • ••

• •+

+

• •

••

••

••

+

O − H  → → CH 3 − O •• + CH 3 − O − H | | | H CH 3 H ••— • • • •

(c)

O || H−C−H

(d)

CH 3 − N H 2

(e)

(CH3)3CCl + AlCl3 → (CH3)3C+ + –AlCl4

(f)

CH2 = CH2 + BF3 → B F3 − CH 2 − C H 2

+

O | • → → H − C − H • NH 3  | + NH 3

••

+

••

CH 3 − CH 2 − •C• l••

+

—

 → →

CH 3 − N H 2

− CH 2 CH 3 +

• •

••

—

C l•• ••

+

(g)) (g (h)

—

+

—

+

B F3 − CH 2 − C H 2 + CH2 = CH2 → B F3 − CH 2 − CH 2 − CH 2 − C H 2

(i) Q.9

Pred Pr edic ictt the the prod produc ucts ts of of the the follo followin wing g acid acid_b _bas asee reac reactio tions ns.. – H2SO4 + CH3COO l

Q.10 Q.10 (a)) (a

Methyl Meth ylli lith thiu ium m (C (CH H3Li) is often used as a base in organic reactions. Pred Pr edic ictt the the pro produ duct ctss of of the the fol follo lowi wing ng ac acid id – bas basee rea react ctio ion. n. CH3CH2 – OH + CH3 – Li → What is is the conjugate acid of CH CH3Li ? Would you expect CH 3Li to be a strong base or a weak base ?

(b)) (b Q.11

Which reagent Which reagent in each each pair pair listed listed here here would would be the the more react reactive ive Nu in in a protic protic solven solventt ? – ⊕ (a) CH3NH or CH3NH2 (b) H2O or H3O – – (c) CH3O or CH3COO (d) CH3SH or CH3OH (e) Ph3N or Ph3P (f) CH3COO– or –OH (g) H2S or HS– (h) NH3 or NH4⊕

Q.12 Q.1 2

Each of these these molecules molecules is electrophile. electrophile. Identify the electrophili electrophilicc atom & draw a mechanism mechanism for reaction reaction with a generalised nucleophile Nu–, giving the product in each case. (a)


(b)

(c)

(d) Cl – Cl

(e)


[3] [3 ]

Q.13

Each of these molecu Each molecules les is nucleop nucleophile hile.. Identify Identify the nucleo nucleophil philic ic atom & draw a mechan mechanism ism for reactio reaction n + with a generalised electrophile E , giving the product in each case. (a) R – C ≡ C–

(b)

(d)

(e)

(c) NH2 – NH2

Q.14

Arrange Arra nge the the followi following ng compo compounds unds in order order of of increas increasing ing basic basicity ity..

(a)

CH3NH2, CH3 NH3⊕ , CH3NH–

(b)

CH3O–, CH3NH–, CH3 CH 2−

(c)

CH3CH = CH–, CH3CH2 CH 2− , CH3C≡C–

Q.15

Neither of these these methods methods of of making making pentan-1,4 pentan-1,4 diol will work. Explain why not not – what what will happen instead?

(i)

CHO–CH2–CH2–CH2–OH

    →

Br–CH2–CH2–CH2–OH

Mg

(ii)

Q.16

MeMgBr

followed by H +

 →  Et 2O

CH 3 − CH − CH 2 − CH 2 − CH 2 | | OH OH

MgBr–CH2–CH2–CH2–OH

CH CHO

3     →

followed by H

+

Suggest what Suggest what specie speciess would would be be formed formed by each each of the the following following combin combinations ations : – (a) PhO + CH3COOH + CH3COO –

(b)

(c) Pyridinium ion + trifluoroacetate ion Q.17 Q. 17

Say which pk a belong to which functional group in case of following amino acids :

(i)

cysteine :

(ii)

glu luta tam mic ac acid id :

Q.18

Record Reco rd the follow following ing sets of compo compounds unds acco according rding to incre increasin asing g pKa ( = – log Ka)

(a)) (a (b) (c)) (c (d)) (d (e)) (e

,

: 1.8, 8.3 & 10.8

: 2.1 .19, 9, 4.2 .25 5, 9. 9.6 67

, cy cycl cloh ohex exan anee carb rbox oxyl ylic ic aci cid. d.

1-b -bu utyne, 1-butene, butane Prop Pr opan anoi oicc acid acid,, 3-br 3-brom omop opro ropa pano noic ic aci acid, d, 2-n 2-nitr itrop opro ropa pano noic ic aci acid d Phe heno nol, l,oo-ni nitr trop ophe heno nol, l, o-c -cre reso soll Hex exy yla lam min inee, ani nili lin ne, me meth thy yla lam min inee



[4] [4 ]

Q.19

Expla Ex plain in whic which h comp compou ound nd is the the wea weake kerr base base..

(a)

or

(b)

CH2 = CH – CH = CH – CH2– or CH2 = CH – CH2–

(c)

O O || || − O − C − C − OH or

(d)

Q.20

O O || || HO − C − C − OH

or

Rank Ran k the the follow following ing amin amines es in incre increasin asing g basic basic natu nature. re.

(a) (i)

(ii)

(iii)

(iv)

(i)

(ii)

(iii)

(iv)

(i)

(ii)

(iii)

(b)

(c)

Q.21 (a) (a) (b)

Dimethyl furmamid Dimethyl furmamidee (DMF) is an an example example of polar polar aprotic aprotic solvent solvent,, aprotic aprotic meaning meaning it has no no hydrogen hydrogen atoms attached to highly electronegative atoms. Draw Dr aw wh what at you you pre predi dict ct to to be be its its most most imp impor orta tant nt res reson onan ance ce fo form rms. s. DMF when when use used d as the the react reaction ion solv solvent ent,, greatl greatly y enhan enhances ces the reac reactivi tivity ty of nucl nucleop eophil hiles. es. e.g. e.g. NaCN + CH3CH2Br → CH3CH2 C ≡ N + NaBr Suggest an explanation for this effects.

Q.22 (a)

Arrange Arran ge the the basic basic stren strength gth of of the follo followin wing g compou compounds nds.. – – – OH CH3COO Cl (i ) (ii) (iii)

(b)

CH ≡ C– (i)

CH2 = CH– (ii)

CH3CH2– (iii)

(c)

CH2 = CHCH2NH2 (i)

CH3CH2CH2NH2 (ii)

CH ≡ C – CH2NH2 (iii)



[5] [5 ]

(d) (i)

(ii)

(iii)

(i)

(ii)

(iii)

(e)

(f)

Cl– (i)

RCOO– (ii)

Q.23

Set the fol follow lowing ing in inc increa reasin sing g orde orderr of of pk pk b :

(i)

OH– (iii)

RO– (iv)

NH2– (v)

,

(ii)

CH3NH2 , (CH3)2 NH , (CH3)3 N , NH3

(iii)

,

(iv) Q.24

[In aqeous medium]

, Arrange Arra nge the foll followin owing g in inc increa reasing sing aci acid d stren strength gth :

(a)

(i)

(ii)

(b)

CH3– OH (i)

(c)

(iii)

(ii)

O || CH 3 − C − OH (i)


(iii)

O O || || HO − C − C − OH (ii)

O O || || HO − C − CH 2 CH 2 − C − OH

(iii)


[6] [6 ]

Q.25 (i)

Set the fol follow lowing ing in inc increa reasin sing g orde orderr of pk a : Meth Me than anee su sulf lfon onic ic ac acid id,, ac acet etic ic ac acid id & me meth than anol ol..

(ii)

CH3– CH2 – CH3 , CH2 = CH – CH3 , CH3 – CHO , CHO – CH 2 – CHO , CH 4

(iii)

CH3NO2 , (NO2)2 – CH2 , (NO2)3 – CH

(iv)

(v)

,

,

CH3COOH , NO2– CH2 – COOH , CH 3 − C − CH 2 − C − OH || || O O

(vi)

, H

(vii)

,

H

, H

H

CHO – CH2 – CHO , CH 3 − C − CH 2 − C − CH 3 , Et − O − C − CH 2 − C − O − Et , || || || || O O O O Et − O − C − CH 2 − C − CH 3 || || O O

Q.26 Q.2 6 (a) (b)

Cya yani nicc aci cid d (H (HO– O–C C≡N) & isocyanic acid (H–N=C=O) differ in the positions of their electrons but their structure do not represent resonance structures. Explain Losss of a prot Los proton on from from cyani cyanicc acid acid yield yieldss the same same ani anion on as as that that obtain obtained ed by by loss loss of a proto proton n from from isocyanic acid. Explain.

Q.27

Draw a me Draw mech chan anis ism m for for this this rea react ctio ion. n. PhCHBrCHBrCO2H + NaHCO3 → PhCH=CH–Br + CO2

Q.28

Arrange Arran ge the the increas increasing ing order order of acidic acidic streng strength th of the followin following g compoun compounds. ds.

(a) (i)

(b)

(iii)

CH2=CH–CH2CO2H (i)

(c)

(ii)

CH3OH (i)


CH3CH2CO2H

(ii) CF3OH (ii)

(iii) CCl3–OH (iii)


[7] [7 ]

Q.29

Expl Ex plai ain n whi which ch is a str stron onge gerr aci acid. d. O O || || (b) CH 3 − C − CH 3 & CH 3 − C − CH 2CN

(a) CH3CH3 BrCH2NO2

OH

OH

(c)

or

(d) O=C–CH3

O=C–CH3

(e)

Q.30

or

or

Which Whic h of the the follow following ing woul would d you pred predict ict to to be the the stron stronger ger acid acid ?

(a)

or

(b)

CH3 – CH2 – CH2 – OH or CH3 – CH = CH – OH

(c)

CH3 – CH = CH – CH 2 – OH or CH3 – CH = CH – OH

Q.31

Which Whic h is a stro strong nger er bas base? e? & Wh Why y. (a) ethylamine or aniline (c) phenoxide ion or ethoxide ion

(b) ethylamine or ethoxide ion (d) cyclohexylamine or aniline

Q.32

The Ka of phenylacetic acid is 5.2 × 10 –5, and the pK a of propionic acid is 4.87.

(a) (b) (c)

Calculate the pKa of phenylacetic acid and the K a of propionic acid. Whic ich h of of th these is is th the str stro onger ac acid? Predic Pre dictt wheth whether er the the foll follow owing ing equ equilib ilibriu rium m will will favor favor the rea reacta ctants nts or the the prod product ucts. s.

Q.33 Q.3 3

Explain Expla in why why the 2-meth 2-methylpyrr ylpyrrolidine olidine boils at a higher higher tempe temperature rature than its isomers isomers N- methylpy methylpyrrolidi rrolidine. ne.

Q.34

Although nitration Although nitration usually usually causes causes elevat elevation ion of B.P. B.P. yet the nitration nitration of resorcino resorcinoll to 2-nitroresorci 2-nitroresorcinol nol decreases their B.P. then their parent compound.

Q.35

o-nitrophenol is sparingly o-nitrophenol sparingly soluble soluble in in water & has lower B.P B.P. but p-nitroph p-nitrophenol enol is comple completely tely soluble soluble in water & has high boiling point.

Q.36

When 30 ml of ethanol ethanol and and 5 ml of water are are mixed the the volume volume of of the resulting resulting solution is less less than 35ml. Explain.



[8] [8 ]

Q.37 Q.3 7

Ammonium Ammo nium salts salts are are much much more solub soluble le in water water than than are the corres correspond ponding ing sodium sodium salts. salts. Explain Explain??

Q.38

HF has a dipole dipole momen momentt of 1.82 D, D, its boiling boiling point point is 19.34° 19.34°C. C. Ethyl Ethyl fluoride fluoride has has an almost almost identica identicall diploe moment & has a larger molecular weight, yet its B.P. B.P. is – 37.7°C. Explain. Explai n.

Q.39

HCO2H & CH3CO2H exists as dimer. Explain.

Q.40

Cycloh Cyc lohexa exanol nol is is more more solubl solublee in water water then then 1-h 1-hexa exanol nol..

Q.41 Q. 41

Explain wh why CH CH3OH and CH3CH2OH are reasonably good solvents for many ionic compounds compare the solvent properties of ethanol and pentanol towards ionic compound.

Q.42

1,5-Pe 1,5 -Penta ntaned nediol iol is solu soluble ble & 1-Pen 1-Pentan tanol ol is sligh slightly tly solub soluble le in H2O.

Q.43

Compare Comp are the the relative relative (i) Boiling Boiling point pointss & (ii) Water Water solubili solubilities ties of of toluene toluene & phenol. phenol.

Q.44

Which Whi ch isome isomerr (o, m or or p) of hydr hydroxa oxacet cetoph opheno enone ne steam steam disti distills. lls.

Q.45

Give structu structure re for ethanol ethanolamine amine showin showing g two different different intramo intramolecu lecular lar H–bonds H–bonds & discu discuss ss their their relative relative strength.

Q.46

Which Whi ch of the the follow following ing syst system em show show H–bon H–bonding ding duri during ng tautom tautomeris erism. m.

(a)

(b)

(c)

(d)

Q.47

Trans Tr ans isome isomerr of indigo indigotin tin is stab stable le w.r w.r.t .t cis cis isomer isomer.. Explain. Explain.

Q.48

What is the the attackin attacking g site of conju conjugate gate base base of triketo triketo form of of phlorogluc phloroglucinol inol in protic protic & aprotic aprotic solve solvent. nt.

Q.49

In each each of the the foll followi owing ng pair pairss which which is more more sta stable ble :

(a)

(b)

l

(c)

(e)


l

(d)

l

l

l


[9] [9 ]

Q.50

In each each of the the foll followi owing ng pair pairss which which is less less sta stable ble :

(a)

(b)

l

(c)

(e) Q.51

(d)

l

l

l

l

In each each of the the foll followi owing ng pair pairss which which is more more sta stable ble :

(a)

(b)

(d)

Q.52

(c)

l

(e)

l

l

In each each of the the foll followi owing ng pair pairss which which is less less sta stable ble :

(a)

(c)

B ansal C lass l asses es

l

l

(b)

(d)

l

l

Q. Ba Bank nk on Ac Acid idit ityy, Ba Basi sici city ty,, HH-Bo Bond ndin ing g & Tau auto tome meri rism sm

[10] [1 0]

Q.53

In each each of of the follo following wing pair pairss which which will will have have highe higherr enol enol content content : (a) CH3CHO and

(c)

(b)

and

(d)

and

(e)

Q.54

and

In each each of the the followin following g pairs pairs which which will have have less enol cont content ent : (a)

and

(b)

and

(c)

and

(d)

and

(e) CH 2 | Cl Q.55

and

− CHO

and CH 3 − CHO

In each each of of the follo following wing pair pairss which which will will have have highe higherr enol enol content content :

(a) CH − CHO and CH 2 − CHO 2 | | Cl NO 2 (c)

(d)


(b)

and

and

and


[11] [1 1]

Q.56

In each each of the the followin following g pairs pairs which which will have have less enol cont content ent :

(a)

Q.57

(c)

and

(e)

and

Q.59

(d)

and

(e)

(a)

(b)

(d)

(e)

(c)

Which Whi ch of of the foll followin owing g compo compound undss can can exhib exhibit it tautoi tautoimeri merism sm :

(b)

(c)

(d)

(e)

Which Whic h of the the follow following ing comp compoun ounds ds can can not not exhib exhibit it tautoim tautoimeris erism m:

(a)

(d) Q.61

and

Which Whic h of the the follow following ing comp compoun ounds ds can can not not exhib exhibit it tautoim tautoimeris erism m:

(a) Q.60

(b)

Which of Which of the foll followin owing g compo compound undss can can exhib exhibit it tautoi tautoimeri merism sm : (a) CH2 = C = O (b) CH2 = CH CH – OH (c (c)) HO HO – CH = CH CH – OH

(d) CH3CN Q.58

and

(b)

(c)

(e) CH3 – NO

What is the relationsh relationship ip between between these these two two molecules? molecules? Discus Discusss the structure structure of the anion anion that that would would be formed by the deprotonation of each compound.



[12] [1 2]

Q.62 Q.6 2

5,5 – dimethylc dimethylcyclo yclohexa hexane ne –1,3 –dione –dione (dimedon (dimedone) e) shows shows tautomerism tautomerism.W .Write rite down tautome tautomeric ric structure. structure.

Q.63

Draw enol enol forms forms of these these carbonyl carbonyl compo compounds unds and comment comment on the stabilit stability y of the the enol forms.

(a)

Q.64

The propor proportion tion of enol enol in a sample sample of the two two ketones ketones below below are show shown. n. Why are are they so different different ?

(a)

Q.65

(b)

4 × 10–4 % enol

(b)

62 % enol

(a) and an d (b) Shows tautomeric forms of (a) & (b).

Q.66

Isatin Isa tin was was the firs firstt compo compound und to show show tau tautom tomeris erism. m.

What is the tautomeric form of isatin. i satin. Q.67

1, 3 – dicarbony dicarbonyll compounds compounds such such as (A) are usually usually mostly mostly enolized. enolized. Why is this ? Draw Draw the enols available to compounds A & B comment on the different pattern of enolization.

(A) Q.68

(B)

In each each of the the follow following ing sets sets of of compoun compounds ds write write the the inc increas reasing ing order order of of % enol enol content content

(a)

(b)



[13] [1 3]

(c)

(d)

(e)

Q.69

In each each of the followi following ng sets sets of compou compounds nds write write the decr decreas easing ing order order of % enol enol content. content.

(a)

(b)

(c)

(d)

(e)



[14] [1 4]

Q.70

Q.71

Enol form form of cyclobuta cyclobutanone none is very unstabl unstablee vs enol enol form of triketoc triketocyclob yclobutan utane, e, which which is very stabl stable. e.

has lower boiling point than

even when former has – OH group.

Q.72 Among these give ease of enolization. Q.73

% enol enol content content of acetyl acetylacet acetone one in followin following g solvent solventss is found as : Solvent % enol content H2O 15 Liquid state 76 hexane 92 gas phase 92 Explain the observation.

Q.74

Explain the observation.

Q.75

l

This tautomeric system exist almost exclusively in favour of phenol and it is insensitive to change in solvent.



[15] [1 5]

ANSWER KEY Q.2 Q.3 Q.5 Q.6 Q.7 Q.11 Q.1 1 Q.14 Q.1 4 Q.18 Q.19 Q.1 9 Q.20 Q.22 Q.23 Q.24 Q.2 4 Q.25 Q.28 Q.28 Q.29 Q.2 9 Q.30 Q. 30 Q.31 Q.3 1 Q.32 Q. 32 Q.49 Q.4 9 Q.50 Q.5 0 Q.51 Q.5 1 Q.52 Q.5 2 Q.53 Q.5 3 Q.54 Q.5 4 Q.55 Q.5 5 Q.56 Q.5 6 Q.57 Q. 57 Q.58 Q.59 Q.60 Q.68 Q.69 Q.72

LA b,e LB acdf (a) 2; (b) 1; (c (c) 1 CH3CH3 + CH3C ≡ CMgBr (a)) 1; (a 1; (b) (b) 1; (c (c)) 1; 1; (d) (d) 1; (e (e)) 2; 2; (f) (f) 1 (a)) 2; (a 2; (b) (b) 1; (c (c)) 1; 1; (d) (d) 1; (e (e)) 1; 1; (f) (f) 3 (a) 1; 1; (b) 1; 1; (c) 1; 1; (d) 1; 1; (e) 2; 2; (f) 2; 2; (g) 2; 2; (h) 1 (a) 2<1< 2<1<3; 3; (b) (b) 1<2< 1<2<3; 3; (c) (c) 3<1<2 3<1<2 (a) 3<2<1 3<2<1;; (b) 1<2<3 1<2<3;; (c) 3<2<1; 3<2<1; (d) (d) 2<1<3; 2<1<3; (e) 2<3<1 2<3<1 (a) 2; (b) (b) 1; 1; (c) (c) 2; 2; (d) (d) 2 (a) 3<2 3<2<1<4 <1<4;; (b) (b) 1<2<3 1<2<3<4; <4; (c) 3<1< 3<1<2 2 (a) 1>2>3; 1>2>3; (b) 1<2<3; (c) (c) 3<1<2; (d) 2<1<3; 2<1<3; (e) 1<2<3; (f) (f) 1<2<3<4<5 1<2<3<4<5 (i) 1>2; 1>2; (ii) (ii) 4>3>1 4>3>1>2; >2; (iii) (iii) 1<2; (iv) 1<2 (a) 1<2< 1<2<3; 3; (b) (b) 3>1> 3>1>2; 2; (c) (c) 1<3<2 1<3<2 (i) 1<2<3; 1<2<3; (ii) 1>5>2>3 1>5>2>3>4; >4; (iii) (iii) 1>2>3; (iv) (iv) 1>3>4>2; 1>3>4>2; (v) 1>3>2; 1>3>2; (vi) 2>1>3; 2>1>3; (vii) 3>4>2>1 (a) 3>1> 3>1>2; 2; (b) (b) 1>2> 1>2>3; 3; (c) (c) 2>3>1 2>3>1 (a) 2; (b) (b) 2; 2; (c) 1; (d) (d) 1; 1; (e) (e) 1 (a)) 2; (a 2; (b) (b) 2; (c (c)) 2 (a) 1; (b) (b) 2; 2; (c) (c) 2; 2; (d) (d) 1 4.25 4. 25,, 1. 1.34 34×1 ×10 0 –5 (a) 2; (b) (b) 2; 2; (c) 1; (d) (d) 1; 1; (e) (e) 1 (a)2; (a) 2; (b) (b) 2; 2; (c) (c) 2; (d) 2; (e) (e) 1 (a) 2; (b) (b) 2; 2; (c) 1; (d) (d) 2; 2; (e) (e) 1 (a) 2; (b) (b) 1; 1; (c) (c) 1; 1; (d) (d) 1 (a) 1; (b) (b)1; 1; (c) (c) 2; (d (d)1; )1; (e) 2 (a) 1; (b) (b) 1; 1; (c) 2; (d) (d) 1; 1; (e) (e) 2 (a) 1; (b) (b) 1; 1; (c) (c) 1; 1; (d) (d) 1 (a) 2; (b) (b) 2; 2; (c) 2; (d) (d) 1; 1; (e) (e) 2 a, b, c, c, d, d, e a, c, d b b (a) 2>1>4>3 2>1>4>3;; (b) 3>2>1; 3>2>1; (c) 3>2>1 3>2>1;; (d) 3>1>2; 3>1>2; (e) 3>1>2 3>1>2 (a) 3>1>2; 3>1>2; (b) 4>2>1>3; 4>2>1>3; (c) 4>3>1>2; 4>3>1>2; (d) 1>3>4>2; 1>3>4>2; (e) 3>2>4>1 3>2>4>1 3>1>2



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