TONE-UP YOUR MEMORY –ORGANIC REASONING by akpanda

CL-XII –CHEM : BRUSH UP WITH SOME ORGANIC CONCEPTS . [ORGANIC _MLL]

MM - 10 , Time allowed – 15 minutes
Name -------------------------- Roll no -------- Marks scored --------------
CARD-1
1 # Which is more Reactive towards nucleophile by SN2 . ( 1-bromopentane , 2-bromopentane )
2# Which is more acidic – ( O-methoxy phenol , o-nitro phenol )
3# Which is more basic . ( N-ethyl ehanamine , ethyl amine )
4# Which has more Boiling point (n-propyl chloride , isopropyl chloride)
5# Which is more Reactive towards HCN (i.e nucleophilic addition reaction ) ( Acetal dehyde , propanone)
6# Which is more Reactive towards nucleophile by SN1 . ( cyclohexyl chloride , allyl chloride)
7# Which is more Reactive towards electrophile ( nitrobenzene , anisole)
8# Which has more bond angle ( Methanol ,Methoxy methane )
9# Which has more Boiling point ( Methanol , methanamine)
10# Which compound undergoes faster SN1 reaction? ( Tert-butyl chloride and 3-chloropentane )

CARD-2

11# Which is more easily hydrolysed by aqueous KOH and why? (C6H5CH2Cl and C6H5CHClC6H5 )
12# Gabriel phthalimide synthesis is preferred for synthesizing pure ------- and why? ( aliphatic primary amines .aromatic primary amines)
13# Which one is more soluble in water and why? (Ethylamine , aniline)
14# Whose pKb is more and why ? ( aniline , methylamine )
15# Which one does not undergo Friedel-Crafts reaction and why and why? ? ( Phenol , aniline )
16# Which has higher boiling point in isomeric cases and why ? (primary amines, tertiary amines )?
17# Which is more easily nitrated and why and why? ? ( Benzene and Phenol)
18# Which is steam volatile and why? ( Ortho-nitrophenol , Para-nitrophenol)
19# Which is more acidic and why? ( Phenol , ethanol )
20# Which is more acidic and why? (ortho-nitrophenol , para -nitrophenol)

CARD-3

21# Which is preferred for the preparation of alkyl chloride from alcohol and why? ( thionyl chloride , PCl5 , Lucas Reagent)
22# Which is less reactive towards nucleophilic substitution reaction and why? ?( C6H5Cl and C6H11Cl)
23# Which is more stable and why? ( Diazonium salts of aromatic amines , Diazonium salts of aliphatic amines) .
24# Which is more easily dehydrated and why? ( sec-alcohol , tert-alcohol )
25# # In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction and why? ?

26# In the following pairs of halogen compounds, which would undergo SN2 reaction faster and why? ?

27# Pure primary amines are prepared through ( ammonolysis method , Gabriel phthalimide Synthesis)
28# Which acid of each pair shown here would you expect to be stronger and why? ?
(i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H
(iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H (iii) F3C—C6H4—COOH or H3C—C6H5—COOH
29# Whose dipole moment is more and why? ( chlorobenzene , Cyclohexyl chloride )
30#Which shows more reactivity in nucleophilic addition reactions and why? . (Di-tert-butyl ketone, Methyl tert-butyl ketone)
CARD-4

31# Which has lowest Kb and why? (Aniline , p-nitroaniline and p-toluidine)
32# Which has highest boiling point and why? ? (Pentan-1-ol , n-butane, pentanal , ethoxyethane.)
33# Which shows optical activity and why? ( 2-bromobutane , 1-bromobutane)
34# Which has higher Melting point and why? ( p-dichlorobenzene , O-dichlorobenzene)
35# Which should be kept in closed dark coloured bottle and why? ? ( Chloroform , iodoform)
36# Which one shows highest reactivity towards HCN and why ? (Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone. )
37# Which one has highest dipole moment and why? ( CH2Cl2 , CHCl3 , CCl4)
38# Which one easily get nitrated ? ( Benzene , Phenol , Chlorobenzene , Nitrobenzene)
39# Which one will react faster in SN2 reaction with OH ˉ and why? (i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl
40# “Greater the stability of carbocation , greater will be its ease of formation from alkyl halide and faster will be the rate of reaction”—
This statement better suits for ( 10 ,20 ,30 –halide) which leads to (SN2 , SN1) Reactions exclusively .
 CARD-5
41# Which is more acidic .( 2-methyl propan-2-ol , Butan-2-ol )
42# Which has highest basic character in aq. phase ? [ C2H5NH2, (C2H5)2NH, (C2H5)3N and NH3 ]
43# Which one forms cyanohydrin in good yield and why? ( 2,2,6-trimethylcyclohexanone , Cyclohexanone)
44# Which is less acidic and why ? ( ethyl amine , ethyl alcohol)
45# Which is a stronger base and why ? ( aliphatic amine , aromatic amine)
46# Which is better leaving group ( chloride or iodide )
47# Which has the highest boiling point and why ? ( Bromomethane, Bromoform, Chloromethane, Dibromomethane)
48# Which would undergo SN2 reaction faster and why ? ( 1-chloro -1-cyclohexyl methane and cyclohexyl methane )
49# Which has more reactive towards nucleophilic substitution reaction ( Chlorobenzene , cyclohexyl chloride)
50# Which one will undergo racemisation when treated with aq. KOH in polar solvent and why ?
( Vinyl chloride ,methyl chloride , 2-chlorobutane )
CARD-6
51# Which has the most acidic character and why ?(Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid )
52# Which is more acidic and why ? (a) (F3C—C6H4—COOH or H3C—C6H5—COOH) (b) (CH3CO2H or CH2FCO2H )
53# Which is more reactive towards Lucas Reagent ( Propanol , isopropyl alcohol)
54# Which will undergo Friedel Craft reaction . ( Anisole , Aniline)
55# Which is less acidic and why? ( Methanamine , Methanol)
56# Which is more reactive towards HCN and why? ( Acetone , Acetaldehyde , Formaldehyde , Di-tert-butyl ketone)
57# Which is more acidic and why? ( Benzoic acid , 4-nitro benzoic acid , 4-methoxy benzoic acid )
58# Which has higher boiling point and why? ( ethanol , propane , propanoic acid , methoxymethane)
59# Which has highest solubility in water and why ? ( C6H5NH2, (C2H5)2NH, C2H5NH2)
60#Which has highest acidic character ( Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.)
CARD-7
61# Which has higher boiling point in isomeric cases and why ? ( p-amines , t-amines)
62# Which one is preferred for preparing chloroalkanes from alcohol. ( PCl 5 , SOCl2)
63# Which has higher boiling point and why? (Propanol , butane , propanone , Methoxy ethane )
64# Which one is more stable and why ? ( phenyl carbocation , benzyl carbocation , methyl carbocation , dimethyl carbocation )
65# Among the following most stable conjugate base is -----( phenoxide , acetate , fluoroacetate , 2-Fluoropropanoic acid , benzoate , trifluoroacetate )
66# Which one is easily reacts with aq. KOH at room temperature ? ( 2,4 –dinitro chlorobenzene , 3,5 –dinitro chlorobenzene)
67# Which one will not gives foul smelling substance when treated with chloroform and alcoholic KOH ?
( Aniline ,N-Mthyl methanamine , Ethanamine )
68# Which one shows turbidity immediately when treated with conc. HCl and anhyd. ZnCl 2 and why ? ( Butanol , butan-2-ol , tert-butyl alcohol )
69# Which is more reactive towards aq.NaOH ( Chlorobenzene , 1-chloro-2-nitrochlorobenzene)
70# Which one will respond positive iodoform test and why ¿ (Etanol ,Methanol)
CARD-8
71# Which one undergo Canizzaro’s reaction .( Acetaldehyde , Benzaldehyde)
72# Which one undergo Aldol condensation themselves ( acetaldehyde , formaldehyde)
73# What is the Major product of Etard’s Reaction ( Salicylic acid , benzaldehyde)
74# What could be the product of Gabriel Pthalimide reaction ( Aniline , methyl amine)
75# Ethanol is converted to ethane in presence of conc.H2SO4 at what temp. ( 413K ,443K)
76# Which reagent is used when phenol is converted into 2,4,6-tribromophenol ( Br 2 in CS2 , Br2 in Water )
77# What is the Major product of Reimer –Tiemann Reaction . ( Salicylic acid , Salicyldehyde)
78# Which one will give the iodoform test ( acetophenone , benzophenone)
79# Which is a mild oxidizing agent ( KMnO4 /H+ , PCC)
80# The major products formed 2-methyl -2-methoxy propane reacts with HI are --------------------------- and ---------------------
CARD-9
81# Identify the major alkenes when the following alkyl halides with sodium ethoxide in ethanol ( or sodium in alcohol)
(a) 1-Bromo-1-methylcyclohexane ------------------------------------------------------------------------------
(b) 2-Chloro-2-methylbutane -------------------------------------------------------------------------------------------
(c) 2,2,3-Trimethyl-3-bromopentane.-------------------------------------------------------------------------------------
82# Which one gives alcohol when treated with Nitrous acid ? ( Aniline and Ethanamine )
83# Which one give white precipitate when treated with aq. KOH and AgNO 3 solution ? ( Vinyl chloride , allyl chloride )
84# Name the products which is obtained when ethyl magnesium bromide reacts with propanol . -------------------------
85# Give one use of (a) Freon ----------------------- (b) Iodoform ----------------------- (c) Chloroform ----------- (d) DDT --------------
86# Which alcohol one is most easily dehydrated in acidic condition and why ? ( primary , secondary , tertiary )
87# Write the IUPAC name and one use of the product obtained when Salicylic acid is treated with acetic anhydride? ---------------
88# Write the major product of (a) Reimer-Tiemann reaction : ----------------------------------
(b) Gatterman –Koch Reaction : ---------------------------------- © Kolbe’s Reaction :----------------------------------------------------
89# When phenol is treated with ----------------------- gives white precipitate and why ? ( Br 2 in CS2 , Bromine water )
90# Which one cannot undergo aldol condensation and why ? ( Acetophenone , acetaldehyde , benzaldehyde , acetone )
CARD-10
91# Write the product when acetaldehyde is treated with semicarbazide --------------------------------------------------
92# During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester
should be removed as soon as it is formed. It is because -----------------------------------------------------------------------------------------
93# Phenol is converted to 2,4,6-tribromophenol when treated with ( Br 2 in CS2 , Br2 water) .
94# Predict the major product of acid catalyzed dehydration of (a) 1-methyl cyclohexanol : ------------------- (b) Pentan-2-ol : ----------------------------
95# Grignard reagents should be prepared under anhydrous conditions because ---------------------------------------------------------------------
96# Haloalkanes react with KCN to form alkyl cyanides as the main product because -------------------------------------------------------------
97# H2SO4 cannot be used along with KI in the conversión of an alcohol to an alkyl iodide because ---------------------
98# Write the major products when 2-bromopentane is treated with alcoholic KOH : ------------------------------------ + ------
99# When anisole is treated with HI , the major products are --------------------------------------------------------------
100# When 2-methyl -2-methoxy propane is treated with HI , the major products are -----------------------------------
101# write the major products when 2-methyl -2-bromo propane is treated with sodium phenoxide ----------------------------------------------
 FOR REVISION- EXAM SPECIAL ORGANIC REASONIG QUESTIONS-II (5M)
ARRAGE THE FOLLOWING WITH THE PROPERTIES MENTIONED*** BY A K PANDA
1 # Arrange the following in increasing order of their basic strength:
(i) C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2 and (C2H5)2NH
(ii) C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2
(iii ) CH3NH2, (CH3)2NH, (CH3)3N, C6H5NH2, C6H5CH2NH2.
(iv) C6H5NH2, C6H5N(CH3)2, (C2H5)2NH and CH3NH2
(v) Aniline, p-nitroaniline and p-toluidine
(vi) C6H5NH2, C6H5NHCH3, C6H5CH2NH2.
(vii) C2H5NH2, (C2H5)2NH, (C2H5)3N and NH3 (in gas and aq.phase)
(viii) Explain the observed Kb order : Et2NH > Et3N > EtNH2 (a) in aqueous solution & (b) in gas phase ?
(ix) In decreasing order of the Kb values: C2H5NH2, C6H5NHCH3, (C2H5)2NH and C6H5NH2
Q.2#Which acid of each pair shown here would you expect to be stronger?
(i) CH3CO2H or CH2FCO2H (ii) CH2FCO2H or CH2ClCO2H (iii) CH2FCH2CH2CO2H or CH3CHFCH2CO2H
(iii) F3C—C6H4—COOH or H3C—C6H5—COOH
Q.3 # Arrange the following compounds in increasing order of their acid strength:
(i) Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.
(ii) ethanol , water, ethanoic acid , phenol
(iii) p-methoxy phenol , p-nitrophenol, phenol .
(iv) CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH, (CH3)2CHCOOH, CH3CH2CH2COOH
(v) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid
Q.4# Arrange the following compounds in increasing order of their reactivity in nucleophilic addition reactions.
(i) Ethanal, Propanal, Propanone, Butanone.
(ii) Benzaldehyde, p-Tolualdehyde, p-Nitrobenzaldehyde, Acetophenone.
(iii) Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN)
Q.5# Arrange the following compounds in increasing order of their boiling points.
(i) CH3CHO, CH3CH2OH, CH3OCH3, CH3CH2CH3
(ii) CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2-O-C2H5, CH3CH2CH2CH2CH3
(iii) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol. (iv) Pentan-1-ol , n-butane, pentanal , ethoxyethane.
(v) Acetaldehyde , ethanol , acetone , propane . (vi) Acetic acid , methyl formate , acetamide , propan-1-ol
(vii) diethylether, butanoic acid , butanol. (viii) Bromomethane, Bromoform, Chloromethane, Dibromomethane.
(ix) 1-Chloropropane, Isopropyl chloride, 1-Chlorobutane. (x) C2H5OH, (CH3)2NH, C2H5NH2
(xi) In increasing order of solubility in water: C6H5NH2, (C2H5)2NH, C2H5NH2.
Q.6# Predict the order of reactivity of the following compounds in S N1 and SN2 reactions:
(i) The four isomeric bromobutanes (ii) C6H5CH2Br, C6H5CH(C6H5)Br, C6H5CH(CH3)Br, C6H5C(CH3)(C6H5)Br
Q.7# Arrange the compounds of each set in order of reactivity towards SN2 displacement:
(i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane
(ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane
(iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 2-Bromobutane,
Q.8# Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism? Explain your
answer

Q.9# In the following pairs of halogen compounds, which would undergo SN2 reaction faster?

Q.10# In the following pairs of halogen compounds, which compound undergoes faster SN1 reaction?

Q.11# write the major products formed by heating each of the following ethers with HI
(a) C6H5-CH2—O—C6H5 (b) CH3—CH2—CH2—O—C(CH3)2—CH2—CH3
(c) CH3—CH2—CH(CH3)-- CH2—O—CH2—CH3 (d) 2-methyl -2-methoxy propane (e) Anisole
Q.12# Identify the major alkenes when the following alkyl haides with sodium ethoxide in ethanol
(i) 1-Bromo-1-methylcyclohexane (ii) 2-Chloro-2-methylbutane (iii) 2,2,3-Trimethyl-3-bromopentane.
CBSE MOST WANTED !!!!!!!---
ORGANIC REASONING QUESTIONS ON CARDS FOR 2016
ORGANIC REASONING CARD-I
**Q.1 # Why pKb of aniline is more than that of methylamine .
OR ,
why are Aliphatic amines stronger bases than aromatic amines ?
Q. 2# Ethylamine is soluble in water whereas aniline is not . Why?
Q.3 # Methylamine in water reacts with ferric chloride to precipitate
hydrated ferric oxide.
**Q.4 # Amino group is o,p-directing for aromatic electrophilic
substitution . Why does aniline on nitration gives a
substantial amount of meta-nitroaniline ?
**Q.5# Aniline does not undergo Friedel-Crafts reaction
(alkylation and acetylation) (PN-395)
ORGANIC REASONING CARD-II
Q.6# Diazonium salts of aromatic amines are more stable than those
of aliphatic amines.
**Q.7# Gabriel phthalimide synthesis is preferred for synthesising
primary amines.
**Q.8 # Why cannot aromatic primary ammines be prepared by
Gabriel phthalimide synthesis .
Q.9# Why are amines less acidic than alcohols of comparable
molecular masses .
*Q.10# Why do primary amines have higher boiling point than
tertiary amines ?
ORGANIC REASONING CARD-III
**Q.11 # Cyclohexanone forms cyanohydrin in good yield but
2,2,6-trimethylcyclohexanone does not.
**Q.12# There are two –NH2 groups in semicarbazide. However,
only one is involved in the formation of semicarbazones.
(Hint: Consider steric effect and electronic effect )
**Q.13# During the preparation of esters from a carboxylic acid
and an alcohol in the presence of an acid catalyst, the water
or the ester should be removed as soon as it is formed.
***Q.14# Although phenoxide ion has more number of resonating
structures than carboxylate ion, carboxylic acid is a
stronger acid than phenol. Why?
**Q.15# Haloalkanes react with KCN to form alkyl cyanides as
main product while AgCN forms isocyanides as the chief
product. Explain.
ORGANIC REASONING CARD-IV
**Q.16# Phenylmethyl ether reacts with HI to give phenol and methyl
iodide and not phenyl iodide and CH3OH .
**Q. 17# Explain why
(i) the dipole moment of chlorobenzene is lower than that of cyclohexyl
chloride?
(ii) alkyl halides, though polar, are immiscible with water?
(iii) Grignard reagents should be prepared under anhydrous conditions?
(iv) Why chloroform is kept in closed dark coloured bottle completely
filled ?
Q.18# Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily
hydrolysed by aqueous KOH.
*Q.19# p-Dichlorobenzene has higher m.p. and solubility than those of
o- and m-isomers. Discuss.
Q.20# The treatment of alkyl chlorides with aqueous KOH leads to the
formation of alcohols but in the presence of alcoholic KOH, alkenes
are major products. Explain.
ORGANIC REASONING CARD-V
*Q.21# Why iodination of alkane carried with oxidizing agent ?
**Q.22# Why haloarenes are less reactive towards nucleophilic
substitution reaction ?
**Q.23# Why electron withdrawing group at ortho- and para-
position increased the reactivity of haloarenes ?
*Q.24# Why thionyl chloride is preferred for the preparation of
alkyl chloride from alcohol ?
Q.25# Explain why is ortho-nitrophenol more acidic than ortho-
methoxy phenol .
ORGANIC REASONING CARD-VI
Q.26# Explain how does the -OH group attached to a carbon of
benzene ring activates it towards electrophilic substitution
reaction .
**Q.27# Explain the fact that in aryl alkyl ethers
(i) the alkoxy group activates the benzene ring towards
electrophilic substitution reaction , and
(ii) it directs the incoming substituents to ortho- & para-
position in benzene ring .
Q.28# Ortho-nitrophenol is steam volatile but its para isomer is not ?
Q.29# Phenol is more acidic than ethanol ?
Q.30# Explain why is propanol higher boiling point than butane ?
ORGANIC REASONING CARD-VII
Q.31# Explain why are alcohols comparatively more soluble in
water than the corresponding hydrocarbons ?
Q.32# Why are amines less acidic than comparable alcohols ?
OR, Why are amines more basic than alcohols ?
**Q.33# Although chlorine is an electron withdrawing group, yet it
is ortho-, para- directing in electrophilic aromatic substitution
reactions. Why?
Q.34# Why sec- & tert- alkyl halides are not used during
Williamson’s Synthesis .
Q.35 # The relative ease of dehydration of alcohols follows :
tert-OH > sec-OH > primary alcohol .
ORGANIC REASONING CARD-VIII
Q.36 # Of Benzene and Phenol, which is more easily nitrated and
why ?
Q.37 # Although haloalkanes are usually prepared from alcohols ,
haloarenes can’t be prepared from phenols.
*Q.38 # Give reason for the higher boiling point of ethanol in
comparison to methoxy methane ?
**Q.39# Preparation of ethers by acid dehydration of secondary and
tertiary alcohols is not a suitable method . Give reason .
Q.40# Why is sulphuric acid not used during the reaction of
Alcohols with KI?
CBSE MOST WANTED !!!!!!!---
ANSWERS TO ORGANIC REASONING QUESTIONS ON CARDS
**** ANSWERS- Card-I ****
ANS-1- It is because in aniline or other arylamines, the -NH2 group is attached directly to the benzene ring. It results in the unshared electron pair on
nitrogen atom to be in conjugation with the benzene ring and thus making it less available for protonation.
Aniline is a resonance hybrid of the following five structures.

On the other hand, anilinium ion obtained by accepting a proton can have only two resonating structures (kekule).

We know that greater the number of resonating structures, greater is the stability. Thus you can infer that aniline (five resonating structures) is more stable
than anilinium ion. Hence, the proton acceptability or the basic nature of aniline or other aromatic amines would be less than that of ammonia.
Alternative Answer—In aromatic amines , the lone pair on nitrogen participates in resonance with the benzene ring and electron density decreases .
Hence electron donation capacity decreases and hence less basic character .
In case of methyl amine , +I-effect group ( CH3--) donates electron to the nitrogen and electron density increases on nitrogen , so ,it has high basic
character .
ANS-2- Lower aliphatic amines are soluble in water because they can form hydrogen bonds with water molecules. However, solubility
decreases with increase in molar mass of amines due to increase in size of the hydrophobic alkyl part.
** Non-polar part ( C6H5-) predominates over polar part( -NH2)
Higher amines are essentially insoluble in water.
ANS-3- When methyl amine reacts with water releases hydroxide ion . which reacts with Fe3+ of FeCl3 and forms Fe(OH)3 .
CH3NH2 + H2O  CH3N+H3 + OH ˉ
CH3N+H3 OH ˉ + FeCl3  3 (CH3N+H3 ) Cl ˉ + Fe(OH)3
ANS-4I In the strongly acidic medium, aniline is protonated to form the anilinium ion which is meta directing. That is why besides the
ortho and para derivatives, significant amount of meta derivative is also formed.
ANS-5-Aniline does not undergo Friedel-Crafts reaction (alkylation and acetylation) due to salt formation with aluminium chloride, the
Lewis acid, which is used as a catalyst. Due to this, nitrogen of aniline acquires positive charge and hence acts as a strong deactivating
group for further reaction.
**** ANSWERS- Card-II ****
ANS-6- Primary aliphatic amines form highly unstable alkyldiazonium salts . Primary aromatic amines form arenediazonium salts which
are stable for a short time in solution at low temperatures (273-278 K). The stability of arenediazonium ion is explained on the basis of
resonance.

ANS-7- Because we obtain pure primary amines in Gabriel phthalimide synthesis which is not possible in ammonolysis .
ANS-8 - Aromatic primary amines cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with
the anion formed by phthalimide. Due to resonance it developes partial double bond character between aromatic carbon and nitrogen.
ANS-9- The conjugate bases of alcohol i.e alkoxide ion is more stable than conjugate bases of amine i.e amide (R─NH ˉ ) , due to
higher electronegativity of oxygen than nitrogen .
ANS-10- Primary and secondary amines are engaged in intermolecular association due to hydrogen bonding between nitrogen of one and
hydrogen of another molecule. This intermolecular association is more in primary amines than in secondary amines as there are two
hydrogen atoms available for hydrogen bond formation in it.
Tertiary amines do not have intermolecular association due to the absence of hydrogen atom available for hydrogen bond formation.
Therefore, the order of boiling points of isomeric amines is as follows: Primary > Secondary > Tertiary
 **** ANSWERS- Card-III ****

ANS-11- This is an nucleophilic addition reaction . Here CN ˉ acts as a nucleophile which experience more steric hindrance because of
presence of bulky groups which surrounds the carbonyl group while attacking the carbonyl ( >C=O ) group in 2,2,6-
trimethylcyclohexanone than Cyclohexanone .
ANS-12- The NH2 attached to >C=O in –CO-NH2 of semicarbazide ( H2N—NH-CONH2 ) loses its nucleophilic character through
resonance by participating its lone pair electrons with >C=O . So , it will have less tendency for participation in nucleophilic addition reaction .
ANS-13- It is a reversible reaction . In order to suppress the backward reaction to occur and making the forward reaction favorable for
the formation of ester the water or the ester should be removed as soon as it is formed. According to Le Chatelier’s Principle .
Answer-14-The higher acidity of carboxylic acids as compared to phenols can be understood similarly.
The conjugate base of carboxylic acid, a carboxylate ion, is stabilised by two equivalent resonance structures in which the negative
charge is at the more electronegative oxygen atom.
The conjugate base of phenol, a phenoxide ion, has non-equivalent resonance structures in which the negative charge is at the less
electronegative carbon atom. Therefore, resonance in phenoxide ion is not as important as it is in carboxylate ion. Further, the negative
charge is delocalised over two electronegative oxygen atoms in
carboxylate ion whereas it is less effectively delocalised over one oxygen atom and less electronegative carbon atoms in phenoxide ion .
Thus, the carboxylate ion is more stabilised than phenoxide ion, so carboxylic acids are more acidic than phenols.
ANS-15- KCN is predominantly ionic and provides cyanide ions in solution. Although both carbon and nitrogen atoms are in a position to
donate electron pairs, the attack takes place mainly through carbon atom and not through nitrogen atom since C—C bond is more stable
than C—N bond. However, AgCN is mainly covalent in nature and nitrogen is free to donate electron pair forming isocyanide as the main
product.
**** ANSWERS- Card-IV****
ANS-16-In case of anisole, methylphenyl oxonium ion, C6H5 ─O+H—CH3 is formed by protonation of ether. The bond between O–CH3
is weaker than the bond between O–C6H5 because the carbon of phenyl group is sp2 hybridised and there is a partial double bond
character .
Therefore the attack by I ˉ ion breaks O–CH3 bond to form CH3I. Phenols do not react further to give halides because the sp2 hybridised
carbon of phenol cannot undergo nucleophilic substitution reaction needed for conversion to the halide.
ANS--17(i) The lone pair electrons of chlorine in benzene participates in resonance with the conjugated system and oppose the bond
dipole of C—Cl bond . This cancellation makes it lower dipole moment which is not the case in case of cyclohexyl chloride .
(ii) In order for a haloalkane to dissolve in water, energy is required to overcome the attractions between the haloalkane molecules and
break the hydrogen bonds between water molecules. Less energy is released when new attractions are set up between the haloalkane and
the water molecules as these are not as strong as the original hydrogen bonds in water.
As a result, the solubility of haloalkanes in water is low.
****However, haloalkanes tend to dissolve in organic solvents because the new intermolecular attractions between haloalkanes and
solvent molecules have much the same strength as the ones being broken in the separate haloalkane and solvent molecules.
(iii) Grignard reagent reacts with water Grignard reagents are highly reactive and react with any source of proton to give
hydrocarbons.
Even water, alcohols, amines are sufficiently acidic to convert them to corresponding hydrocarbons.
It is therefore necessary to avoid even traces of moisture from a Grignard reagent. On the other hand, this could be considered as one of the
methods for converting halides to hydrocarbons.
(iv) Chloroform is slowly oxidised by air in the presence of light to an extremely poisonous gas, carbonyl chloride, also known as
phosgene.
ANS-18- C6H5CHClC6H5 , the carbocation forms here is more resonance stabilised due to presence of two phenyl ring.
ANS-19-It is due to symmetry of para-isomers that fits in crystal lattice better as compared to ortho- and meta-isomers.
ANS-20- When a haloalkane with β-hydrogen atom is heated with alcoholic solution of potassium hydroxide, there is elimination of
hydrogen atom from β-carbon and a halogen atom from the α-carbon atom. As a result, an alkene is formed as a product.

**** ANSWERS- Card-V ****

ANS-21 - Because the HI which is produced is a strong reducing agent , that can reduce R—I into alkane . So , to prevent the reverse reaction , oxidizing
agent ( e.g HIO3) is added to consume the HI and nullify the backward process.
ANS-22- The following factors are responsible for that
(i) C—Cl bond acquires a partial double bond character due to resonance .
(ii) The SP2 hybridised carbon with more electronegativity hold the electron pair of C—Cl bond more tightly .
(iii) The phenyl carbocation is not stabilsed by resonance .
ANS-23 - Electron withdrawing group at ortho- and para- position withdraws the electron density forom the benzene ring and thus facilitates the attack of
the nucleophile on haloarene.
The negative charge appear at ortho- and para- positions with respect to the halogen substituent is stabilized by
electron withdrawing group (--NO2) , while in case of m-nitrobenzene , none of the resonating structure bear the negative charge on carbon atom bearing the –NO 2 group.
ANS-24—Because the byproducts are escapable gases ( HCl And SO 2)
Ans-25:- O-nitro phenoxide ion is more stable than ortho-methoxy phenoxide ion . ( Nitro group electron-withdrawing )
The presence of electron withdrawing groups such as nitro group, enhances the acidic strength of phenol, by stabilizing its conjugate base.. It is due to the
effective delocalisation of negative charge in phenoxide ion by the presence of electron withdrawing nitro group. On the other hand, electron releasing
groups, such as alkyl groups, in general, do not favour the formation of phenoxide ion resulting in decrease in acid strength This effect is more
pronounced when such a group is present at ortho and para positions
 *** ANSWERS- Card-VI ****

.Ans-26:- The –OH group attached to the benzene ring activates it towards electrophilic substitution. Also, it directs the incoming group to
ortho and para positions in the ring as these positions become electron rich due to the resonance effect caused by –OH group.
Ans-27-(i) Due to +R –effect the lone pair present on oxygen participate in resonance with the conjugated system ( i.e benzene ring)
and increases the electron density at ortho- and para- positions . So, electrophile being electron deficient can attack easily the aromatic ring
and reactivity increases.
(ii) As the electron density increases at ortho- and para- positions , the incoming electrophile attaches at these two positions .
Ans-28:- o-Nitrophenol is steam volatile due to intramolecular hydrogen bonding while p-nitrophenol is less volatile due to intermolecular
hydrogen bonding which causes the association of molecules
Ans-29:- Due to resonance stabilization of phenoxide ion, it is more stable than ethoxide ion.
Ans-30:- The high boiling points of alcohols are mainly due to the presence of intermolecular hydrogen bonding in them which is lacking
in ethers and hydrocarbons
**** ANSWERS- Card-VII ****

Ans-31:- Solubility of alcohols and phenols in water is due to their ability to form hydrogen bonds with water molecules
The solubility decreases with increase in size of alkyl/aryl (hydrophobic) groups
Ans-32:- Because Oxygen is more electronegative than Nitrogen. The O—H bond is more polar than N—H bond.
For basic character Oxygen has more tendency to retain electron pair rather than donating it.
Ans-33- Chlorine withdraws electrons through inductive effect and releases electrons through resonance. Through inductive effect,
chlorine destabilises the intermediate carbocation formed during the electrophilic substitution.
Through resonance, halogen tends to stabilise the carbocation and the effect is more pronounced at ortho- and para- positions. The
inductive effect is stronger than resonance and causes net electron withdrawal and thus causes net deactivation. The resonance effect tends
to oppose the inductive effect for the attack at ortho- and para positions and hence makes the deactivation less for ortho- and para attack.
Reactivity is thus controlled by the stronger inductive effect and orientation is controlled by resonance effect.
Ans-34:- In case of secondary and tertiary alkyl halides, elimination competes over substitution. If a tertiary alkyl halide is used, an alkene
is the only reaction product and no ether is formed. For example, the reaction of CH3ONa with (CH3)3C–Br gives exclusively 2-
methylpropene. It is because alkoxides are not only nucleophiles but strong bases as well. They react with alkyl halides leading to
elimination reactions
Ans-35:- An electron-releasing group (–CH3, –C2H5) increases electron density on oxygen tending to decrease the polarity of O-H bond.
This decreases the acid strength. For this reason, the acid strength of alcohols decreases as given in question.

**** ANSWERS- Card-VIII ****

Ans-36:-Phenol because the –OH group attached to the benzene ring activates it towards electrophilic substitution
Ans-37:- Because the carbon of phenyl group is sp2 hybridised and there is a partial double bond character due to resonance
Ans-38 :- Ethanol get associated with H-bonding but methoxy methane does not .
ANS-39--The method is suitable for the preparation of ethers having primary alkyl groups only. The alkyl group should be unhindered
and the temperature be kept low. Otherwise the reaction favours the formation of alkene. The reaction follows SN 1 pathway when the
alcohol is secondary or tertiary. However, the dehydration of secondary and tertiary alcohols to give corresponding ethers is unsuccessful
as elimination competes over substitution and as a consequence, alkenes are easily formed.
Answer-40-H2SO4 cannot be used along with KI in the conversion of an alcohol to an alkyl iodide as it converts KI to corresponding HI
and then oxidizes it to I2.