Reasoning Questions in Organic Chemistry Text Exercise

By: Er.
Purushottam Pal Organic Chemistry
REASONING QUESTIONS IN ORGANIC CHEMISTRY

TEXT EXERCISE
1. Why is sulphuric acid is not used during reaction of alcohols with KI?
Ans: Sulphuric acid converts the KI into HI and then oxidizes into I2
2. Arrange each set of compounds in order of increasing boiling poings.
(i) Bromo Ethane , Bromoform, Chloro methane, Dibromo methane
(ii) 1-Chloro Propane, Isopropyl chloride, 1-chloro butane
Ans: Chloro Methane(CH3Cl) < Bromo Ethane(CH3-CH2-Br) < Dibromo
Mehane(CH2Br2) < Bromoform (CHBr3)
CH3CHCl-CH3 < CH3-CH2-CH2Cl < CH3-CH2-CH2-CH2-Cl
As atomic mass increases boiling point increases. And branching compounds has less
spherical contact as compare with straight chain compounds. Hence bp less
for branching chain alkyl halides.
3. Which of the following undergo SN2 faster?
(i) Cl CH2Cl
(i) I Cl
Ans: CH2Cl is more faster under go SN2 because it is Primary alkyl halide
I is more faster to under go SN2 mechanism because I is better

leaving group due to its large size.
4. Predict the order of reactivity of the following compounds in SN1 & SN2 reactions.
(i) The four isomeric bromo butanes
(ii) C6H5CH2Br, C6H5CH2 (C6H5 )Br, C6H5CH2 (CH3)Br, C6H5CH2 (CH3 )(C6H5 )Br
Ans: CH3-CH2-CH2-CH2-Br< CH3- CHCH3- CH2- Br < CH3-CH2-CHBr –CH3<
C(CH3)3Br order for SN1 mechanism
CH3-CH2-CH2-CH2-Br> CH3- CHCH3- CH2- Br > CH3-CH2-CHBr –CH3>
C(CH3)3Br order for SN2 mechanism
C6H5CH2Br< C6H5CH (CH3)Br< C6H5CH (C6H5 )Br< C6H5C (CH3 )(C6H5 )Br
Order for SN1 mechanism
C6H5CH2Br> C6H5CH (CH3)Br> C6H5CH (C6H5 )Br> C6H5C (CH3 )(C6H5 )Br
Order for SN2 mechanism
5. Although Chlorine is an electron with drawing group yet it is orho para directing in
electrophilic aromatic substitution reactions. Why?
Ans: Cl is electron with drawing by inductive effect, and it electron relesing by resonance
and creates negative charge at ortho and para positions. And here resonance effect
is more as compare with inductive effect.
6. Which alkyl halide from the following pairs would you expect to react more rapidly
by an SN2 mechanism? Explain your answer?
1. CH3-CH2-CH2-CH2-Br & CH3-CH2-CHBr –CH3
2. CH3-CH2-CHBr –CH3 & C(CH3)3Br
3. CH3- CHCH3- CH2- CH2- Br & CH3- CH2- CHCH3- CH2- Br
Ans: 1. CH3-CH2-CH2-CH2-Br primary alkyl halide is more reactive than secondary
alkyl halide
2. CH3-CH2-CHBr –CH3 Secondary alkyl halide is more reactive than Tertiary
alkyl halide
3. CH3- CHCH3- CH2- CH2- Br As methyl group is far from Br it will less stabilize
the carbo cations and facilitate the SN2 mechanism.
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By: Er. Purushottam Pal Organic Chemistry
7. Which of the following compound go faster SN1 reaction:
1. &
Cl
2. & Cl
Ans: 1. first compound ismore stable because tertiary is more reactive than secondary
alkyl halide for SN1 mechanism.
2. . first compound is more stable because Secondary is more reactive than
primary for SN1 mechanism.
8. Which one of the following has highest boiling point;
CH2Cl2 CHCl3 CCl4
Ans: net Dipole moment of CH2Cl2 & CCl4 is zero due to cancellation dipole moment of
bonds due to its symmetric structure. Where as net dipole moment of CHCl3 is not
zero. Because its structure is not symmetric.
9. Which compound in each of the following pairs react faster in SN2 reaction with OH?
(i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl
2
Ans: CH3I is faster reactive by SN mechanism because C-I bond strength is less than
C-Br bond
CH3Cl is faster reactive than (CH3)3CCl by SN2 mechanism because 10 alkyl halide
more reactive by SN2 mechanism.
10. Halo alkanes react with KCN to form alkyl cyanides as main product while AgCN
forms isocyanides as the chief product. Explain.
Ans: 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 not through nitrogen atom since C—C is
more stable than C—N bond. However, AgCN is mainly covalent in natrue and
nitrogen is free to donate electron pair forming isocyanide as the main product.
11. Why does NO2 group show its effect only at ortho and para positions and not at meta
positions?
Ans: The presence of NO2 group at ortho and para positions with draws the electron
density form the benzene ring and thus facilitates the attact of the nucleophile on halo arene. The
carbanaion thus formed is stabilized through resonance. The negative charge appeared at ortho
and para positions with respect to the halogen substituent is stabilized by NO2 group while in
case of meta nitro benzene, none of the resonating structures bear the negative charge on carbon
atom bearing the NO2 group. There fore the presence of nitro group at meta position does not
stabilize the negative charge and no effect on reactivity isobserved by the presence of NO2 group
at meta position.
12. The dipole moment of chloro benzene is lower than that of cyclohexyl chloride.Why?
Ans: It is due to electron with drawing effect of phenyl group which decrease dipole
moment of chloro benzene.
13. Alkyl halides, though polar, are immiscible with water. Explain.
Ans: Due to absence of hydrogen bond in alkyl halides with water.
14. Grignard reagent should be prepared under anhydrous conditios. Give reason.
Ans: Grignard reagent highly react with water to alkanes.
RMgX + H2O  R—H + MgXOH
15. Vinyl chloride is less reactive towards nucleophilic substitution. Explain.
Ans: Due to resonance between C—Cl bond in vinyl chloride show partial double bond
character.
CH2=CH—::Cl:
16. Chloroform stored in dark colored bottles by completely filling it it. Explain.
Ans: Chloroform react with air in presence of sun light it forms poisonous phosogene.
2 CHCl3 + O2  2 COCl2+ 2 HCl
17. Out of C6H5CH2Cl & C6 H5CHCl C6H5 Which is more easily hydrolyzed by KOH?
Ans; The second comound is more resonance stabilized hence easily forms carbo cation
and react faster by SN1 mechanism.
18. The treatment of alkyl halides with aqueous KOH leads to the formation of alcohols
but in the presence of alcoholic KOH alkenes are major products. Explain
Ans: Substitution of alkyl halide gives alcohols and elimination gives alkenes and there is
a competition between substitution and elimination. In the presence of low polarity
solvent like alcohol favours elimination where as in the presence of high polarity
solvent like water substitution favored.
19. Bond angle of ethers is slightly greater than tetrahydral bond angle. Explain.
Ans: due to repulsion of bulky alkyl groups in ethers bond angles is slightly greater than tetrahydral
bond angle.
20. Arrange the following sets of compounds in order of their increasing

boiling points:
(a) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.
(b) Pentan-1-ol, n-butane, pentanal, ethoxyethane.
Ans: (a) Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.
(b) n-Butane, ethoxyethane, pentanal and pentan-1-ol.
21. Acidity of alcohols is as fallows explain? 10>20>30
Ans: 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 in the following
order:
22. Arrange the following compounds in increasing order of their acid strength:
Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.
Ans: Propan-1-ol, 4-methylphenol, phenol, 3-nitrophenol, 3,5-dinitrophenol,
2,4, 6-trinitrophenol.
23. The reaction of alcohols with carboxylic acid or anhydrides to form esters conc. H2SO4 is
added, and the reaction with alcohol and acid chloride base like pyridine is used. Explain.
Ans: R-OH + RCOOH/RCOOCOR ↔ RCOOR + H2O
R-OH + RCOCl ↔ RCOOR + HCl
Sulphuric acid removes the water and prevent back ward reaction,
Base like pyridine removes the acid HCl and prevent back ward reaction.
24. The relative dehydration of alcohols is Tertiary>Secondar>Primary give reason.
Ans: Dehydration carryout by carbocation mechanism, and stability of carbocation is
teriary>Secondary>Primary
25. What is intermediate in Riemer –Tiemann reaction.
Ans:
26. Alcohols are comparatively more soluble in water than hydrocarbons of
comparable molecular masses. Explain this fact.
Ans: Due to hydrogen bond
27. Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring
towards electrophilic substitution and (ii) it directs the incoming substituents to ortho and para
positions in benzene ring.
Ans: Methoxy group on Benzene ring donates the electrons and activate the ring and creates –ve
charge on the ortho and para positions hence electrophile is attracted at these positions.
28. Arrange the following compounds in the increasing order of their boiling points:
CH3CH2CH2CHO, CH3CH2CH2CH2OH, H5C2-O-C2H5,
CH3CH2CH2CH2CH3
Ans: CH3CH2CH2CH2CH3 < H5C2-O-C2H5 < CH3CH2CH2CHO <
CH3CH2CH2CH2OH
Alcohols with hydrogen bond has more bp, Ethers have less dipole dipole moment as compare
with aldehydes and alkanes least with weak vander waals forces.
29. Aldehydes and ketones are soluble in water.
Ans: They soluble in water due to formation of H bond between carbonyl compounds and water.
30. Toluene with CrO3 and Acetic anhydride forms benzaldehyde. Explain.
Ans: Touene forms Benzelydine diacetate intermediate with CrO3 and Acetic anhydride.
31. Would you expect benzaldehyde to be more reactive or less reactive in
nucleophilic addition reactions than propanal? Explain your answer.
Ans: The carbon atom of the carbonyl group of benzaldehyde is less electrophilic than carbon atom of
the carbonyl group present in propanal. The polarity of the carbonyl group is reduced in benzaldehyde
due to resonance as shown below and hence it is less reactive than propanal.
32. Carbonyl carbon of carboxylic acid is less electronegative than aldehydes
and ketones give reason.
Ans: The carboxylic carbon is less electrophilic than carbonyl carbon because of the possible
resonance structure shown below:
33. Carboxylic acids are having higher boiling points than aldehydes, ketones and even alcohols
of comparable molecular masses. Explain.
Ans: Carboxylic acids are higher boiling liquids than aldehydes, ketones and even alcohols of
comparable molecular masses. This is due to more extensive association of carboxylic acid molecules
through intermolecular hydrogen bonding. The hydrogen bonds are not broken completely even in the
vapour phase. In fact, most carboxylic acids exist as dimer in the vapour phase or in the aprotic
solvents.
34. Carboxylic acids are stronger acids than pheonol thought both possess
resonance stabilization of respective anions.
Ans: 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.
35.
Ans: CH2FCO2H because –ve inductive effect by F
CH2FCO2H –ve inductive effect of F is more than Cl
CH3CHFCH2CO2H If –ve inductive group near to COOH more acidic.
-ve inductive effect of three F atoms

36. Give plausible explanation for each of the following:
(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-
Trimethylcyclohexanone does not.
(ii) There are two –NH2 groups in semicarbazide. However, only one is involved
in the formation of semicarbazones.
(iii) 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.
Ans: Due to steric effect and electron releasing effect.
The other two NH2 groups involve resonance with C=O
To prevent back ward reaction
37. Aryl amines cannot be prepared by Gabriel Phthalamide synthesis. Explain.
Ans: Aromatic primary amines cannot be prepared by this method because aryl halides do not
undergo nucleophilic substitution with the anion formed by phthalimide.
38. Boiling point of Primary, secondary and tertiary amines is different give reason.
Ans: 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
39. The basic strength of amines in aqueous solutions is different from gaseous phase give
reason.
It is due to inductive effect, hydrogen bond and hydration effect

40.
41. Generally aniline direct bromination gives tri substituted product to get mono stustitued
product what is to be done.
Ans: This can be done by protecting the -NH2 group by acetylation with acetic anhydride, then
carrying out the desired substitution followed by hydrolysis of the substituted amide to the substituted
amine.
42. Account for the following:

(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated
ferric oxide.
(iv) Although amino group is o– and p– directing in aromatic electrophilic
substitution reactions, aniline on nitration gives a substantial amount of
m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic
amines.
(vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.
Ans: More Pkb less basic, less basisity of aniline is due to involvement of lone pair in
resonance.
In Aneline aromatic nature makes insoluble in water.
CH3NH2 + H2O → CH3NH3+ OH-
These hydroxide ions can make Ferric hydroxie.
in the strongly acidic medium, aniline is protonated to form the
anilinium ion which is meta directing.
Aryl amines can not under go nucleophilic substitution.
43. Give plausible explanation for each of the following:
(i) Why are amines less acidic than alcohols of comparable molecular masses?
(ii) Why do primary amines have higher boiling point than tertiary amines?
(iii) Why are aliphatic amines stronger bases than aromatic amines?
Ans: Nitrogen is less Electronegetive than Oxygen which makes less polarization of
N—H bond as compare with O—H bond.
There is no H bond in Tertiary amines.
In aromatic amines lone pair involve in resonance.
44. Preparation of ethers by dehydration of alcohols is not suitable for the using
of secondary and tertiary alcohols give reason.
Ans: dehydration of secondary and tertiary alcohols to give corresponding ethers is
successful as elimination competes over substitution and as a consequence,
alkenes are easily formed.
45. The following is not an appropriate reaction for the preparation of
t-butyl ethyl ether.
(i) What would be the major product of this reaction ?
(ii) Write a suitable reaction for the preparation of t-butylethyl ether.
C2H5ONa + (CH3)3-Cl → C2H5-O-C(CH3)3
Ans: (i) The major product of the given reaction is 2-methylprop-1-ene.
It is because sodium ethoxide is a strong nucleophile as well as a strong base. Thus elimination
reaction predominates over substitution.
(CH3)3-ONa + C2H5Cl → C2H5-O-C(CH3)3
46. Which of the following is appropriate for the preparation of anisole?

a) Bromo Benzene & Sodium Methoxide b) Phenoxide & CH3Br
Ans: Set b is appropriate because nucleaophilic substitution on aromating ring is difficult due to partial
double bond character.
47. The bond angle in alcohol is slightly less than the tetrahedral bond angle
(109 -28 ). Why Is it so?
Ans: It is due to the repulsion between the unpaired electron pairs of oxygen.
48. Carbon oxygen bond length in phenol is less than the alcohol?
Ands: It is due to the partial double bond character between C and O in phenol.
49. Boiling point of the alcohol is more than the alkenes. Comment?
Ans: due to intermolecular hydrogen in alcohols it has high boiling point.
50. Branched alcohols are having low boiling point compare with normal straight
chain alcohols? Explain. OR
Boiling point t-Butyl alcohol is less than the n-Butyl alcohol? Explain.
Ans: As branching increases surface area decreases and Vander wall’s force decreases, hence
boiling point decreases. And also in branched alcohols due to electron releasing effect strength of
hydrogen decreases.
51. Arrange the following compounds in increasing order of their boiling points?
CH3 -CH2-OH, CH3-CHO, CH3 -O-CH3, CH3 -CH2-CH3,
Ans: molecular of these compounds are similar; ethanol is having inter molecular H- bond hence
more boiling point. Among acetaldehyde and ether, acetaldehyde Has strong di pole attractions than
the ethers. Propene is weak vanderwaal's forces. Hence the boiling point order is
CH3 -CH2- OH> CH3 -CHO > CH3 -O-CH3 > CH3 -CH2 -CH3
52. Arrange the following in increasing order of their relativity towards nucleophilic
addition reactions.
H- CHO, CH3 -CHO, CH3 -CO- CH3
Ans: CH3 -CO-CH3 <CH3-CHO< H-CHO
Electron releasing effect
Steric effect
53. Ethers have low boiling point compare with corresponding alcohols.
Give reasons
Ans: Alcohols can form intermolecular H-bond, where as ethers do not. Hence alcohols are
having high boiling point than ethers.
54. Alcohols are Bronsted bases or Proton acceptors. Explain?
Ans. It is due to presence of unshared electron pair over oxygen atom which
Makes alcohols proton acceptors. Proton acceptors are known as
Bronsted bases.
55. Alcohols are weak acids than water. Explain?
Ans. In both the cases due to polar O-H bond, behave as acids. But in alcohols
due to presence of alkyl groups, which are electron releasing hence O-H
bond is less polarized, shows weak acidic character.
56. Arrange the acidity order for 1, 2 & 3 Isomeric alcohols (C4H10O)?
Ans. Always electron releasing effect destabilizes the anion and decrease the
acidity.
57. Phenol is stronger acid than alcohol. Explain.
(Or)
Phenol is weak proton acceptor than alcohol. Explain.
Ans. Acidity of the substance depends on stability of anion after loosing H+ ion. Since
phenoxide ion undergoes resonance stabilization compare to alkoxide, phenol is more acidic than
alcohol.
58. Arrange the following compounds in increasing order of their acidic strength.
Propan-1-ol, 4-Methyl phenol, Phenol, 3,5 dinitrophenol, 2,4,6
Trinitrophenol.
Ans. Propan-1-ol< 4-Methoxy phenol< Phenol< 3,5 dinitrophenol< 2, 4, 6 Trinitrophenol
Phenol is more than alcohol due to resonance stability of phenoxide ion. Electron releasing
groups like (O-CH3) methoxy decreases acidity. Electron withdrawing groups like (-NO2) nitro
groups increases acidity. More number of electron withdrawing groups more acidity.
59. O- nitro phenol & p-nitro phenol can be separated by distillation? Explain.
Or
Boiling point of p-nitro phenol is more than the o- nitro phenol. Explain?
Ans. O-nitro phenol is a stream volatile due to intermolecular Hydrogen bond where as p-nitro
phenol is having inter molecular Hydrogen bond. Inter molecular hydrogen bond decreases Boiling
point Inter molecular hydrogen bond increases Boiling point
60. The usual halogenations of Benzene takes place of in presence of Lewis acid
catalyst like AlCl3, where as phenol can directly react with Bromine? Explain?
Ans. Incase of Halogenations of benzene Br2 is polarized by FeBr3, but in case of phenol the
polarization of Br2 takes place by phenol due to highly ctivating effect of OH group present on the
benzene ring.
61. (a) Primary alkyl halide reacts with sodium alkoxide and forms ethers in good yield
but t-alkyl halides yield fewer amounts of ethers. Explain?
Ans. Since tertiary carbocation is more stable and it will form alkenes instead of
ether.
(b).Explain the fact that in aryl alkyl ethers (i) alkoxy group activates the benzene ring towards
electrophilic substitution and (ii) it directs the incoming substituents to ortho & para position ?
Ans. Alkoxy group is electron releasing to the benzene ring (+ve mesomeric effect) and by
resonance -ve charge obtained at ortho & para positions only. Hence electrophile attracts at ortho &
para positions. And due to +ve mesomesric effect ring became activated.
62. t- Butyl methyl ether reacts with HI forms methanol & t- butyl iodide explain?
Ans. Since tertiary carbocation is more stable and reaction is following carbocation
mechanism it gives t- Butyl iodide.
63. The commercial ethanol is mixed with copper sulphate & pyridine. Explain.
Ans. Commercial ethanol is mixed with CuSo4 & pyridine to make it unfit for
drinking. It is known as denaturation of alcohol.
64. Explain why are alcohols comparatively more soluble in water than the
corresponding hydrocarbons?
Ans. It is due to Hydrogen Bond formation with water.
65. Explain how does the -OH group to a carbon of benzene ring activates it towards
electrophilic substitution?
Ans. OH group donates its non bonded electrons to resonance with benzene and creates negative
charge at o-p positions hence ring is activated towards electrophilic substitution.
66. Explain the fact that in aryl alkyl ethers (i) alkoxy group activates the benzene ring towards
electrophilic substitution and (ii) it directs the incoming substituents to ortho & para position ?
Ans. Alkoxy group is electron releasing to the benzene ring (+ve mesomeric effect) and by
resonance -ve charge obtained at ortho & para positions only. Hence electrophile attracts at ortho &
para positions. And due to +ve mesomesric effect ring became activated.
67. Unlike phenols, alcohols are easily protanated. Give reason.
Ans. Alcohols act as proton acceptors or Bronsted bases. It is due to presence of
unshared electron pair over oxygen. In case of phenol lone pair is involving
in resonance. Hence, it can not be protanated easily.
68. Reaction of alcohols with hydrogen halides (HX) is of the following order.
Explain. 30 alcohols 20 alcohols 10 alcohols
Ans. This reaction takes place through carbocation mechanism since the stability
of carbocation is 3 2 1. The reactivity order is also same.
69. Anisole react with HI gives phenol & methyl iodide but not iodo benzene and
methanol. Explain.
Ans. Nucleophilic substitution on aromatic ring is difficult due to partial double Bond character
between oxygen and carbon of benzene ring.
70. Name the intermediate or electrophile formed during Reimur-Tiemann reaction?

Ans.Dichloro carbon - :CCl2
71. Phenol react with bromine in the presence of carbon disulphide gives
monobromophenol whereas with water gives tribromophenol. Explain.
Ans. CS2 is a non-polar solvent whereas water is a polar solvent. In the presence of polar solvent
phenol polarizes and gives mole electrophilic substitution.
72. Ethers made of similar kind of polar bonds (symmetric) also posses some net
dipole moment. Explain.
Ans. Due to its bent structure.
73. While separating a mixture of ortho & para nitro phenols by steam distillation, name the
isomer which is Steam volatile. Give reasons?
Ans:O-nitro phenol is steam volatile due to inter molecular hydrogen bond.
74. Explain why O-nitro phenol is more acidic than O-methoxy phenol?
Ans:Nitro group is an electron with drawing which increases acidity where as methoxy group is
an electron releasing which decreases acidity.
75. Phenol is more active towards electrophilic substitution than benzene. Explain?
Ans:OH group present on the phenol is electron releasing and activates the Benzene ring through
resonance.
76. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a
suitable method. Give reasons?
Ans:Secondary and tertiary alcohols will give alkanes easily by dehydration.
77. Explain why is propanal higher boiling than butane?
Ans:Due to intermolecular hydrogen bond present in alcohols,they possess high Boiling point.
78. Explain why are alcohols comparatively more soluble in water than the corresponding
hydrocarbons?
Ans:Due to presence of intermolecular hydrogen bond in alcohols.
79. Aldehydes and ketones possess more dipole moment than ethers. Explain?
Ans:Due to presence of double bond more polarity which increases dipole moment.
34. Arrange the following compounds in increasing order of their boiling points?
CH3-CHO , CH3-CH2-OH , CH3-O-CH3 , CH3-CH2-CH
Ans:Their molecular masses are almost all similar but
CH3-CH2-OH > CH3-CHO > CH3-O-CH3 > CH3-CH2-CH3
Inter molecular more polar than presence of no H-bond &
H-bond ethers polarization
80. Why it is necessary to use sulphuric acid in nitration of benzene?
Ans: sulphuric acid is helping in formation of NO2 electrophile which is easy To substitute on
benzene.
81. Acetic acid is halogenated in the presence of red P and Cl 2 but formic acid cannot be
halogenated in the same way . Explain?
Ans. There is no alpha hydrogen in formic acid.
82. Carboxylic acid are having more boiling point than alcohols of same molecular
mass. explain
Ans. In carboxylic acids strength of H bond is stronger than alcohols and forms
dimmer in carboxylic acids which increases boiling point.
83. Carboxylic acid can not give characteristic reactions of aldehydes and ketones
though both are having carbonyl group CO?
Ans. Carbonyl group in carboxylic acid is resonance stabilized as carboxylate ion . Hence it can
not give nucleophilic addition reactions given by carbonyl group.
84. Formaldehyde gives cannizarros reaction but acetaldehyde cannot . Explain
Ans. Cannizarros reaction is given by any aldehydes without alpha hydrogen hence acetaldehyde
cannot give this reaction.
85. Why do aldehydes and ketones have high dipole moment?
Ans. Due to presence of Polaris able C=O bond in it.
86. Phenol is acidic but do not react with sodium bicarbonate solution. Explain?
Ans. Phenol is a weak acid hence it can not react with weak base like sodium bicarbonate.
87. Boiling point of glycol is higher than alcohol of same molecular mass . Explain?
Ans. As the number of –OH group’s increases strength of H bond increases and boiling point also
increases.
88. Nitration of phenol is easier than benzene .explain?
Ans. Due to presence of –OH group which causes electron releasing effect ,ring is activated and
electrophilic substitution is easier.
89. Why methyl amine has lower boiling point than methanol?
Ans. Amines posses weak hydrogen bond than alcohols , hence methanol has Higher boiling point.
90. Why is it difficult to prepare pure amines by ammonal sis of alkyl halides?
Ans. Reaction of alkyl halides with ammonia gives mixture of amines because Secondary and
tertiary amines also behave as nucleophilic and undergoes substitution with alkyl halides .
91. Electrophilic substitution in case of aromatic amines takes place more readily
than benzene .explain?
Ans. NH2 group present on the benzene is electron releasing and activates ring Hence electrophilic
substitution is easy.
92. Why does silver chloride dissolve in methyl amine solution?
Ans. Methyl amine forms a complex compound with silver chloride and that is
soluble in water
2CH3NH2 + AgCl  [ Ag (CH3NH2)2] Cl
93. Tetiary amines do not undergo acylation .explain?
Ans. As these are not having hydrogen on nitrogen they can not give reaction with acid chlorides.
94. Why is diazotization of aniline carried in ice cold solution?
Ans. Diazonium salts are stable at cold conditions only.
95. Why does amides less basic than amines?
Ans. Lone pair present in amides is involved in resonance hence it is less basic than amines.
96. Why is ethyl amine more basic than amines?
Ans. In ethyl amine lone pair is not involved in resonance where as in aniline lone pair is involved in
resonance. Hence ethyl amine more basic than amines
97. Acid catalyzed dehydration of t- butanol is faster than n-butanol why?
Ans. Dehydration is taking place through carbon cation mechanism as tertiary carbo cation is more
stable .hence t- butanol is faster than n-butanol
98. Sodium bisulphate is used for preparation of aldehydes and ketones?
Ans. Mixture of aldehydes and ketones react with NaHSO3 aldehydes preferably react to form salts as
compare with ketones, hence they are separated.
99. Hydrazones of acetaldehyde are not prepared in highly acidic medium?
Ans. Hydrazones are prepared from hydrazenes and it is basic in nature. In highly
acidic medium it forms salt.
100. Why are amides amphoteric in nature>
Ans. Lone pair present in N of amides in involving in resonance and less available for donating
hence behave as weak bases. And during resonance it forms +ve charge on nitrogen which has
tendency to loose proton and behave as acidic . So amides are amphoteric in nature.
101. Highly branched carboxylic acids are less than unbranched acids .Why?
Ans.As branching increases,electron releasing effect increases,which decreases
acidity.
102. Aneline dissolves in aq.HCl,why?
Ans.Aneline is basic in nature.hence,it is soluble in acids like HCl.
103. A weakly basic solution favours coupling of benzene diazonium chloride with
phenol.Explain?
Ans. In a weakly acidic solution phenol will exist as phenoxide. we know the phenoxide ring is more
activated than phenol itself( due to +R effect).in the aryl coupling reaction phenol will be the
nucleophile and the diazonium salt the electrophile. so increased electron density in the phenoxide ring
will favour coupling.
104. Why are aryl diazonium ion more stable than diazonium ion?
Ans. Aryl diazonium ion is stabilized by resonance but in alkyl diazonium ion ,no
resonance for stabilization.
105. Methyl amine in water reacts with ferric chloride to precipitate ferric
hydroxide.Why?
Ans.Methyl amine is a proton acceptor from water and forms hydroxyl ion which reacts with ferric
ions forms ferric hydroxide.
CH3-NH2 + H2O CH3-NH3+ + OH-
FeCl3 + 3OH- Fe(OH)3 + 3Cl-
106. Ethers possess a dipole moment even if the alkyl radicals in the molecule are
identical.Explain?
Ans.Due to Sp3 hybridisation ,ethers posses bent structure hence net dipole moment
is not zero and will not cancel.
107. Why di-tertiary butyl ethers cannot be prepared by Williamson’s synthesis?
Ans. As tertiary carbocation is more stable,it has less tendency to undergo Nucleophilic
substitution.Hence it cannot be prepared.
108. Treatment of C6H5-CHO with HCN gives a mixture of two isomers which cannot
be separated even by very careful fractional distillation?
Ans.This reaction gives racemic mixture of two optical isomers whichg are having almost all
same boiling point and similar chemical properties .Hence they cannot be separated by fractional
distillation.
109. Electrophilic substitution on nitro benzene is difficult compare with benzene.explain?
Ans.Nitro group present on the benzene is electron withdrawing and deactivates the ring for
substitution.Hence it is difficult.
110. The presence of electron withdrawing groups on benzene facilitates nucleophilic
substitution.Explain?
Ans.Due to electron withdrawing effect it will stabilize the carbanion intermediet.
Trinitrochlorobenzene+KOH Trinitrophenol
111. Tertiary amines are having low boiling point compare with primary and secondary
amines.Explain?
Ans.Due to absence of Hydrogen bond in tertiary amines,they possess low boiling point as compare
with primary and secondary.
112. In solutions,basic strength of amines is secondary>tertiary>primary.Explain?
Ans.Basic strength of amines depends on ammonium cation in solutions .Ammonium stability not only
depends on electron releasing effect but also H-bonding,stearic factor. Hence the above order of basic
strength is correct .
113. In gas phase,basic strength of amines is tertiary>secondary>primary.Explain?

Ans.In gas phase,there is no salvation effect.It only depends on electron releasing effect.Hence the
above order is correct for basic strength in gas phase.
114. Acylation on amines and phenols takes place directly, whereas acylation on benzene
requires AlCl3 catalyst.Give reasons?
Ans.Reaction of amines and phenol with acid chlorides is nucleophilic substitution,which takes place
directly due to presence of lone pair on both oxygen and Nitrogen.Whereas acid chloride on reaction
with benzene is electrophilic substitution which requires a catalyst like AlCl3 catalyst to form an
electrophile.
115. Acid chlorides give pungent smell in air.Explain?

Ans. Acid chlorides undergo hydrolysis with atmospheric moisture and gives HCl fumes,which are
pungent.
116. Nitration of benzene gives substantial amount of meta product,though –NH2 is

o-pdirecting group?
Ans.Nitration takes place in the presence of H+ ions which protanates on Amine and forms which
behaves as electron withdrawing group,hence it forms some amount of meta product.
117. Before nitration,Aneline is acylated.Explain?

Ans.To protect -NH2 group from oxidation and to prevent meta product.
118. Reactivity order of carboxylic acid derivatives are

Acid chlorides>Anhydrides>Esters>Amides.Explain the reason?
Ans.I) Basisity of leaving group
II) Resonance effect
74.Explain cyanides are soluble in water whereas isocyanides are insoluble.
Ans.Cyanides can form hydrogen bond with water whereas Isocyanides cannot.
119. Preparation of Alkyl halides from alcohols by using SOCl2 is preferable.Explain?

Ans.When SOCl2 is used,side products are gases and forms pure alkyl halides.
R-OH+SOCl2 R-Cl + SO2+ HCl
120. Alkyl halides react with nitrites whereas AgNO2 gives Nitro alkanes.Explain?
Ans. KNO2 is an ionic compound and forms NO2- which is an ambidentate nucleophile.It can
form bond with nitrogen and oxygen.Since C-O bond is stable,it forms alkyl nitrites whereas
AgNO2 is covalent compound.Here oxygen is not free.only bonding takes through nitrogen and
forms nitroalkanes.
121. During prepation of esters by reaction of carboxylic acids and alcohols,the ester formed is
distilled out as soon as it is formed.Explain?
Ans.Formation of ester is a reversible reaction.To prevent backward reaction,it is distilled out
immediately.
122. Electrophilic substitution on Benzoic acid takes place at meta position?
Ans.Since COOH group is electron withdrawing group,it acts as meta directing group in
resonance,it creates positive charge on ortho and para position.And electrophile is positive and
feel repulsion at ortho and para position.Hence it goes to the meta position.
SOME REASONING QUESTIONS asked in CBSE Board
2006- DELHI
1. Electrophilic substitution in case of amines takes place more readily than benzene.
2. CH3CONH2 is a weaker base than CH3CH2NH2.
3. Nitro compounds have higher boiling points than hydrocarbons having almost same molecular
mass.
2006- AISSCE
1. σ-nitrophenol is more acidic than σ-methoxyphenol.
2. Glycerol is used in cosmetics.
3. Explain the observed Kb order: Et2NH> Et3N>EtNH2, in aquous solution.
2006- FOREIGN
1. Aldehydes are more reactive than ketones towards nucleophilic reaction.
2. Electrophilic substitution in benzoic acid takes place at meta position.
2005-DELHI
1. Why are primary amines higher boiling than tertiary amines/
2. Alkylamines are stronger base than arylamine.
3. Acetanilide is preferred as good solvent in organic chemistry.
4. Carboxylic acid do not gives characteristic reactions of carbonul group.
5. Treatment of benzaldehyde with HCN gives a mixture of two isomers which can be separated even
by fractional distillation.
6. NaHSO3 is used for purification of aldehydes and ketone.
AISSCE
1. How is the basic strength of aromatic amine affected by the presence of an electron releasing
group on the benzene ring?
2. How an –OH group attached to a carbon in the benzene ring activates benzene towards
electrophilic substitution?
3. Nitrobenzene does not undergo Friedelcraft,s reaction.
4. Methylamine in water reacts with FeCl3 to precipitate Fe(OH)3.
5. Methylamine is stronger base than ammonia.
FOREIGN
1. Why are primary amine higher boiling than tertiary amine?
2. Aldehydes are more reactive than ketones towards.
3. Carboxylic acids have much higher acidity than phenol.
4. In aquous solution, secondary amines are more basic than tertiary amines.
5. Amines are more basic than comparable alcohol.
2004- DELHI
1. Aromatic amines are less basic than ammonia and aliphatic amines.
2. Draw the structure of a carbonyl group and indicate clearly a) hybridized state of carbon, b)
σ-and π- bond present c) electrophilic and nucleophilic centres in it.
3. Aldehydes are more reactive than ketone towards nucleophilic reaction.
4. Chloroacetic acid is stronger than acetic acid.
AISSCE
1. Even in mild condition, aniline on bromination gives 2,4,6-tribromoaniline.
2. Diazonium ion acts as electrophile.
3. Nucleophilic substitution of p-nitrochlorobenzene is easier than that of chlorobenzene.
4. Amines are more basic than comparable alcohol.
5. It is difficult to prepare pure amines by ammonolysis of R-X.
6. Electrophilic substitution in case of aromatic amines takes place more readily than in
benzene.
7. In contrast to arenas, aliphatic hydrocarbons do not undergo nitration.
8. Ethers possess a net dipole moment even if the alkyl radicals in the molecule is identical.
9. Sodium bisulphate is used for purification of aldehydes and ketones.
10. Most aromatic acids are solid but the aliphatic acids are liquid.
11. Aniline is a weaker base than cyclohexyl amine.
12. Benzoic acid is stronger than acetic acid.
********

Reasoning Questions in Organic Chemistry Text Exercise

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Reasoning Questions in Organic Chemistry Text Exercise

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By: Er.

Purushottam Pal Organic Chemistry

REASONING QUESTIONS IN ORGANIC CHEMISTRY

I is more faster to under go SN2 mechanism because I is better

20. Arrange the following sets of compounds in order of their increasing

-ve inductive effect of three F atoms

It is due to inductive effect, hydrogen bond and hydration effect

42. Account for the following:

46. Which of the following is appropriate for the preparation of anisole?

70. Name the intermediate or electrophile formed during Reimur-Tiemann reaction?

113. In gas phase,basic strength of amines is tertiary>secondary>primary.Explain?

115. Acid chlorides give pungent smell in air.Explain?

116. Nitration of benzene gives substantial amount of meta product,though –NH2 is

117. Before nitration,Aneline is acylated.Explain?

118. Reactivity order of carboxylic acid derivatives are

119. Preparation of Alkyl halides from alcohols by using SOCl2 is preferable.Explain?

122. Electrophilic substitution on Benzoic acid takes place at meta position?

SOME REASONING QUESTIONS asked in CBSE Board

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