CBSE Class 12 Chemistry Alcohols Phenole and Ethers
CBSE Class 12 Chemistry Alcohols Phenole and Ethers
CBSE Class 12 Chemistry Alcohols Phenole and Ethers
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174
Chapter 11 to 16
ALCOHOLS, PHENOLS AND ETHERS.
Q.1 Give the IUPAC name of the following.
CH3-C (CH3) =CH-CH2OH
Ans:-3-Methyl But-2-en 1-ol
Q.2 Phenols are much more acidic than alcohols. Why
Ans:-Due to electron with drowning nature of ph-group.
Q3 Give the IUPAC name of the following compound:
.
Solution :
2 − Bromo-3-methyl-but-2-ene-1-ol.
Q.4 What happen when phenol is treated with excess of bromine(aq).
Ans It gives 2,4,6-tribromo phenol.
Q.5 Write chemical equation Williamson synthesis.
Ans- R-X+R- O- Na --------- R-O-R + NaCl
Q.6 Mention one uses of methanol.
Ans – (i) As a denaturant for ethanol
Q.7 The boiling point of ethanol is higher than that methoxy methane.
Ans-Ethanol has inter molecular hydrogen bonding, methoxymehane does not have H-bonding.
Q.8 Name a substance that can be used as an antiseptic as well as a disinfectant.
Ans:
Phenol can be used as an antiseptic as well as a disinfectant. 0.1% Soln of phenol is used as an antiseptic & 1% Soln
of phenol is used as a disinfectant.
Q.9 Write the IUPAC name.
(CH3)3 C-OH
Ans- 2-methyl-2-propanol
Q.10 What is Nucleophiles.
Ans- The species which has high electrons density.
Q.11 Which catalyst are used in Friedel craft reaction?
Ans- Anh.AlCl3.
Q.12 Write a test to distinguish between primary, secondary and alcohols?
Ans Lucas test.
Q13 Write the IUPAC name of CH3OH?
Ans- Methanol.
Q.14 Write the IUPAC name of CH3-O-CH3?
Ans- Methoxy methane.
Q.15.Write the IUPAC name of CH3 CH2-O-CH3?
Ans- Ethoxy methane.
Short answers questions (2marks)
Q3.(i) Explain the mechanism of Addition of Grignard’s reagent to the carbonyl group of a compound forming an
adduct followed by hydrolysis.
(ii) Explain the mechanism of Acid catalysed dehydration of an alcohol forming an alkene.
Ans:
(i) Grignard’s reagent is an alkyl magnesium halide. The alkyl group has a partial negative charge, whereas the
magnesium group has a partial positive charge. The alkyl group attacks the carbon of the carbonyl group to form an
addition compound.
Grignard’s reagent acts as a nucleophilic agent & attacks electrophilic carbon atoms to yield a carbon − carbon bond.
The addition to the nucleophile is an irreversible process due to the high pka value of the alkyl group.
(ii) When heated with concentrated sulphuric acid, phosphoric acid or boric acid, alcohols undergo dehydration to
form alkenes. The mechanism of this reaction involves the protonation of alcohol, followed by loss of a water
molecule & a proton.
(a)
(b)
(c)
During the dehydration of alcohol, the intermediate carbocation may undergo re-arrangement, resulting in the
formation of a stable carbocation.
(iii) Some reactive alkenes like 2 − methyl propene undergo direct hydration in the presence of mineral acids which
act as catalysts. The addition of water to the double bond takes place in accordance with Markonikoff’s rule.
Ans:-(i) Due to presence of a hydrogen attached to oxygen atom. As a result ethanol exists as associated molecules &
hence it has higher bp. than methoxy methane which does not form hydrogen bond.
(ii) Because the phenoxide ion left after the release proton is stabilized by resonance but ethoxide. Moreover
ethoxide ion is destabilized by +1 effect of ethyl group.
(iii) Due to I-effect or R-effect of NO2 gp. The resulting phenolate ion is more destabilized by +1 effect of ethyl gp.
Ans:
5marks questions
Q.1 (a) An Organic compound ‘ A’ with molecular formula C8H8O gives positive DNP and iodoform test. It does not
reduces Tollens or Fehling reagent and doesnotdecolourisesBr2/H2O also.On oxidation with chromic acid gives a
carboxylic acid (B) with molecular formula C7H6O2.Determine the structure of ‘A’ and ‘B’.
Ans-
Q.2 An Organic compound ‘ A’ with molecular formula C3H6 on treatment with aq.H2SO4 gives ‘B’ which on
treatment with HCI/Zncl2 gives ‘C’. Thecompound ‘ C’ on treatment with ethanolic KOH gives back the compound
’A’ .Identify the compound A, B and C .
CH3-CH=CH2---------CH3-CH-CH3------------------CH3-CH-CH2------------------ CH3-CH=CH2
Ans. Aldehydes and ketones can be distinguished by Tollen’s test. Aldehydes give a silver mirror on reacting with
Tollen’s reagent whereas ketones will not react.
Ans. Formaldehyde does not have any α -hydrogen and therefore it cannot show aldol condensation.
3. Carboxylic acids have higher boiling points than alcohols of same no. of carbon atoms?
Ans. Carboxylic acids have more extensive association of molecules through intermolecular hydrogen bonding than
alcohols.
Ans.Pentane-2,4-dione.
7.Write one chemical to distinguish between Formic acid and Acetic acid .
Ans.Formic acid gives silver mirror when treated with Tollen,’s reagent where as acetic acid does not.
Ans.Used as a preservative.
10.Complete the following reactionand give the name of the major product.
CH3CH2OH- Ethanol
HCOOH, ClCH2COOH,CF3COOH,Cl3CCOOH
Ans. CF3COOH>CCl3COOH>ClCH2COOH>HCOOH
RCONH2+4NaOH+Br2 --------
14. Give one chemical test to distinguish between Phenol and benzoic acid.
Ans. On treatment with neutral FeCl3 solution Phenol gives a violet color whereas Benzoic acid does not.
15. Most of the aromatic acids are solids while acetic acids and others of this series are liquids. Why?
Ans. Aromatic acids have higher molecular weights. Therefore more Vanderwaal’s force of attraction as compared to
aliphatic acids and hence they are solids .
1. Would you expect benzaldehyde to be more or less reactive in nucleophilic addition reaction 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 and hence is less reactive.
2. Describe the Transesterification reaction giving an example.
Ans. When an ester reacts with alcohol to form another ester and another alcohol, the process is called trans-
esterification.
Ans. Carboxylic acids having an a α hydrogen atom are halogenated at the α position on treatment with chlorine
or bromine in the presence of small amount of red phosphorous to give α- halocarboxylic acids
(i)X2/P(Red)
RCH2COOH --------------RCH(X)COOH.
(ii) H2O/H+
Ans. (i) Pentan-2-one gives Iodoform test on treatment with I2/NaOHwhere as Pentane -3-one does not.
5.AlthoughPhenoxide ion has more number of resonating structures than Carboxylate ion, Carboxylic acids are more
acidic than Phenol .Why?
Ans. In carboxylate ion (-)ve charge is delocalised over two oxygen atoms whereas in phenoxide ion (-)ve charge is
delocalised over one oxygen atom .Therefore carboxylate ion is more stable than phenoxide ion .That is why
Carboxylic acics are more acidic than Phenol.
6. Why is there a large difference in the boiling points of butanal and butan-1-ol?
Ans:-Butan-1-ol has higher boiling point due to intermolecular hydrogen bonding
7.Name the electrophile produced in the reaction of benzene with benzoyl chloridein the presence of anhydrous
AlCl3. Name the reaction also.
8. Arrange the following in decreasing order of their acidic strength and give reason for your answer.
CH3CH2OH, CH3COOH, ClCH2COOH, FCH2COOH, C6H5CH2COOH
Ans: FCH2COOH > ClCH2COOH > C6H5CH2COOH > CH3COOH >CH3CH2OH
Due to +ve and –Ve inductive effects
9. Write the names associated with the following reactions:-
(i)
(ii)
Ans:
(ii)CH3COO)2Ca ----------------CH3COCH3+CaCO3
(i) CH3CONH2P2O5-/heat-- ?
dil .NaOH
(ii) 2CH3CHO ?
(iii)C6H5COOH HNO3/H2SO4-- ?
dil .NaOH
(ii) 2CH3CHO CH3CH(OH)CH2CHO
(iii)C6H5COOH HNO3/H2SO4—m-O2N-C6H4-COOH
(i)Gatterman-Koch reaction
(iii)Wolf-Kishner Reduction
Ans(i) When benzene or its derivative is treated with carbon monoxide and hydrogen chloride in the presence of
anhydrous aluminiumchloride or cuprous chloride, it gives benzaldehyde or substituted benzaldehyde.This reaction
is known as Gatterman-Kochreaction.
(ii)The carbonyl group of aldehydes and ketones is reduced to CH2 group on treatment with zincamalgam and
concentrated hydrochloric acid called Clemensen Reduction.
(ii)The carbonyl group of aldehydes and ketones is reduced to CH2 group on treatment with hydrazine followed by
heating with sodium or potassium hydroxide in high boiling solvent such as ethyleneglycolcalled Wolff-Kishner
reduction
Ans:
(6).An alkene ‘A’ (Mol. formula C5H10) on ozonolysis gives a mixture of two compounds ‘B’ and ‘C’. Compound ‘B’
gives positive Fehling’s test and also forms iodoform on treatment with I2 and NaOH. Compound ‘C’ does not give
Fehling’s test but forms iodoform. Identify the compounds A, B and C. Write the reaction for ozonolysis and
formation of iodoform from B and C
Ans:
1.An organic compound (A) with molecular formula C8H8O forms an orange-red precipitate with 2,4-DNP reagent and
gives yellow precipitate on heating with iodine in the presence of sodium hydroxide. It neither reduces Tollens’ or
Fehlings’ reagent, nor does it decolourise bromine water or Baeyer’s reagent. On drastic oxidation with chromic acid,
it gives a carboxylic acid (B) having molecular formula C7H6O2. Identify the compounds (A) and (B) and explain the
reactions involved.
Ans:-(A) forms 2,4-DNP derivative. Therefore, it is an aldehyde or a ketone. Since it does not reduce Tollens’ or
Fehling reagent, (A) must be a ketone. (A) responds to iodoform test. Therefore, it should be a methyl ketone. The
molecular formula of (A) indicates high degree of unsaturation, yet it does not decolourise bromine water or
Baeyer’s reagent. This indicates
the presence of unsaturation due to an aromatic ring. Compound (B), being an oxidation product of a ketone should
be a carboxylic acid. The molecular formula of (B) indicates that it should be benzoic acid and compound (A) should,
therefore, be a monosubstituted aromatic methyl ketone. The molecular formula of (A) indicates that it should be
phenyl methyl ketone (acetophenone).
Reactions are as follows:
3. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass of the
compound is 86. It does not reduce Tollens’ reagent but forms an addition compound with sodium hydrogensulphite
and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic acid. Write the possible
structure of the compound.
N=86/86=1
Since hydrogen atoms are double than carbon atoms, therefore, it is likely to be aldehyde or ketone. It does not
reduce Tollen’s reagent so it is a ketone.It reacts with NaHSO3 and gives Iodoform test .Therefore it is
Methylketone.On vigorous oxidation it gives ethanoic acid and propanoicacid .
4.An organic compound (A) molecular formula C8H16O2 was hydrolysed with dil. H2SO4 to give a carboxylic
acid (B) and alcohol (C) . Oxidation of (C) with chromic acid produced (B).(C) on dehydration gives but-1-ene.
Write equations for the reactions involved.
(C)
(C)
Ans: (a).(a) When –CN and –OH groups are attached to the same carbon atom it is called cyanohydrin.e.g.
CH3CH(OH)(CN).
(b) When aldehyde or ketone react with semicarbazide the product formed is semicarbazone. E.g. H3C-CH=N-
NHCONH2
(c) When aldehyde reacts with one mole of alcohol in presence HCl gas Hemiacetal is formed. E.g. H 3C-CH(OH)-
OCH3
(d) When ketones react with two moles of alcohol /; Ethylene glycol in presence of HCl gas Ketal is formed.e.g.
(e)When
aldehyde or ketone reacts with 2,4-DNP orange precipitate is formed.e.g.
: Kolkatta Region
AMINES
Soln: 4-amino-but-1-ene
Q.2 Write structure of methyl amine?
Ans- CH3-NH2
Ans-CH3NC
Q.9 Name one test to distinguish between ethyl cynide and ethyl isocynide.
Ans- ethyl cynide on hydrolysis with acids form propionic acid, whereas ethyl isocynide with dilute HCl
forms ethylamine and formic acid.
Q10.Identify A and B
NaNO2/HCL CuBr
C6H5NH2----------------------A------------------------B
Ans:Hofmann’sbromamide reaction.
Ans:Benzoyl chloride.
2marks questions
Ans:
Basic strength:
Aliphatic amines are stronger bases than aromatic amines due to the presence of lone pair of e- on nitrogen atom. In
case of aromatic amines the lone pair gets delocalised by resonance. Diethyl amine has greater + I effect. Hence, e-
density over the nitrogen atom is more in this case. Similarly N, N − dimethyl aniline has greater + I effect than
aniline.
Ans-
Methyl (−CH3) is an e- donating group. It increases the e- density on the ring. Therefore, the lone pair of nitrogen is
available for donation. Hence, it is most basic. On the other h& nitro (−NO2) is an e- withdrawing group. It decreases
the e- density of the ring. Therefore, the lone pair is more delocalized in this case & is less available for donation.
Thus, it will be least basic among the three.
Ans-
Stronger the base is lesser is the pKb value. (C2H5)2NH is the strongest base due to two e- releasing group followed by
C2H5NH2 which has only one e- releasing group. C6H5NHCH3 is the next stronger base because of the presence of one
e- releasing alkyl group & e- delocalising phenyl group. C6H5NH2 is the least basic wherein the e- get delocalised by
resonance.
Q.4.Write a chemical reaction in which the iodide ion replaces the diazonium group in a diazonium salt.
Ans-:
Ans:
An alkylamine is more basic than ammonia because of inductive effect (+I effect). Alkyl group or ‘R’ has an e--
releasing effect, which increases e- density over nitrogen atom. This increases its basicity.
3marks questions
Ans:
Hofmann’s bromamidereaction: It involves the reaction of bromine with an acid amide in the presence of an alkali. It
results in the formation of a primary amine with one carbon less than the parent compound. Here, the alkyl group
migrates from carbonyl, with the elimination of CO2. For example:
Ans- Gattermanreaction: This is a modification of S&meyer reaction in which benzenediazonium chloride is treated
with copper powder & halogen acid to form aryl halides.
Ans
Coupling reaction: It is the reaction of diazonium salts with phenols & aromatic amines to form azo compounds of
the general formula Ar − N = N − Ar. The coupling of phenol takes place in a mildly alkaline medium.
Ans:
In aniline, the lone pair of e- on the N atom is delocalised over the benzene ring. As a result, the e- density on the
nitrogen atom decreases. In contrast, in CH3NH2, the +I effect of CH3increases the e- density on the N atom.
Therefore, aniline is a weaker base than methylamine. Hence, its pKb value is higher than that of methylamine.
Q.5 Methylamine Soln in water reacts with ferric chloride Soln to give a precipitate of ferric hydroxide.
Ans- Being more basic than water, methylamine accepts a proton from water-liberating OH− ions.
These OH− ions combine with Fe3+ ions present in H2O to form a brown precipitate of hydrated ferric oxide.
5marks questions
Q1.An aromatic compound ‘ A’ on treatment with aqueous ammonia and heating forms compound ‘B ‘ which on
heatiog with Br2 and KOH forms a compound ‘ C’ of molecular formula C6H7N. Write the structures and IUPAC
names of compounds A, B andC.
(III)C6H5NH2 +H2SO4(CONC)---------------
(IV)C6H5N2Cl +C2H5OH------------------------
(V)C6H5NO2 + Fe/HCI----------------------------
Ans:-
(V)C6H5NO2 + Fe/HCI-------------------------------C6H5NH2
5marks questions
Q1.An aromatic compound ‘ A’ on treatment with aqueous ammonia and heating forms compound ‘B ‘ which on
heatiog with Br2 and KOH forms a compound ‘ C’ of molecular formula C6H7N. Write the structures and IUPAC
names of compounds A, B andC.
(III)C6H5NH2 +H2SO4(CONC)---------------
(IV)C6H5N2Cl +C2H5OH------------------------
(V)C6H5NO2 + Fe/HCI----------------------------
Ans:-
(V)C6H5NO2 + Fe/HCI-------------------------------C6H5NH2