PM SHRI KENDRIYA VIDYALAYA, VIRUDHUNAGAR

REVISION ALCOHOLS , PHENOLS, ETHERS L1 BASIC

Q1 Rimer Tiemann reaction is an example of
(i) Nucleophilic substitution reaction ii)Electrophilic substitution reaction
iii)Nucleophilic addition reaction iv)Electrophilic addition reaction
Q2 Which of the following products is formed when benzaldehyde is treated with CH3MgBr and the
additionproduct so obtained is subjected to acid hydrolysis ?
(a) A secondary alcohol (b) A primary alcohol (c) Phenol (d) tert-Butyl alcohol
Q3 Which of the following reagents cannot be used to oxidize primary alcohols to aldehydes?
(i)CrO3in ananhydrous medium. (ii)KMnO4/ H+ (iii)PCC (iv) Heating with Cu at 573K
Q4 Products obtained when benzyl phenyl ether is heated with HI in the mole ratio 1:1 are
(1)phenol (2) benzyl alcohol (3)benzyl iodide (4) iodobenzene
(a) 1 and 3 only (b) 3 and 4 only (c)1 and 4 (d)2 and 4 only
Q5 Ethene reacts with alkaline KmnO4solution to form which substance also used as an Antifreeze.
(a) Glycerol (b) Glycol (c) Propanol (d) Ethanol
Q6 Among the following sets of reactants which one produces anisole?
a)CH3CHO, RMgX (b) C6H5OH, NaOH, CH3I (c) C6H5OH, neutral FeCl3 (d) C6H5CH3
CH3COCl,AlCl3
Q7 The order of acidic strength among the following is
(I) H2O (II) CH3CH2OH (III) C6H5OH (IV) p- Cl C6H4OH
(a) (III>(IV)>(II)>(I) (b) (IV)> (III)> (I)> (II) (c) (IV)>(III)>(II)>(I) (d) (I)>(II)>(IV)>(III)
Q8 (a) Assertion and Reason both are correct and the Reason is a correctexplanation of the Assertion.
(b) Assertion and Reason both are correct but Reason is not a correctexplanation of the Assertion.
© Assertion is correct but reason is wrong statement. (d) Assertion is wrong but reason is correct .
Assertion-The bond angle in ether is less than tetrahedral angle.
Reason- There is strong repulsive interaction between the two bulky (–R) groups in ether
Q9 Assertion: Phenols are more reactive towards electrophilic substitution reaction compared to benzene.
Reason: -OH group in phenol increases the electron density in ortho and para position due to +M effect
Q10 Assertion-Only warm water is required in the formation of picric acid from 2,4,6-trinitrochlorobenzene.
Reason- Presence of three electron withdrawing groups make it unstable.
Q11 Write the Mechanism Acid dehydration of ethanol to yield ethene
Q12 Give simple Chemical test to distinguish between a)Ethanol and methanol.
ii) ethanol,propanol iii) phenol, benzyl alcohol
Q13 Convert i)Phenol to salicylicacid. Ii)Phenol to salicylaldehyde
Q14 How can you convert i)Benzene to phenol , ii)phenol to benzene
Q15 Write the equations for i)Phenol toAnisole ii)Salicylic acid to aspirin iii) Ethylalcohol lto Ethoxyethane
Q16 Write the names of reagents and equations for the preparation of
(i) Ethoxy benzene (ii) 2-Methoxy-2-methylpropane
Q17 Explain the following reactions (i)Reimer-Tiemann reaction (ii)Kolbe’s reaction
Q18 An organic compound(A) with molecular formula C8H16O2 was hydrolysed with dilute sulphuric acid to
give carboxylic acid (B) and an alcohol(C). Oxidation of (C) with chromic acid also produced (B). On
dehydration (C) gives but-1-ene. A. Identify A, B and C. b. Write the chemical equations involved.
Q19 i)(CH3)3C — O C2H5 +HI -→?
(ii) C6H5OC2H5 + HBr -→
Q20 Water , ethanol which is more acidic why ?
 REVISION ALCOHOLS , PHENOLS, ETHERS L2 MEDIUM
Q1 Ethyl alcohol can be prepared from Grignard reagent by the reaction of
(i) HCHO ii)RCN iii)R2CO iv)RCOCl
Q2 Which of the following alcohols undergoes acid catalysed dehydration to alkenes most readily?
(a) (CH3)2CHCH2OH (b) (CH3)3COH (c) CH3CHOHCH3 ( d) CH3CH2CH2OH
Q3 Which of the following alcohols will not undergo oxidation?
Butanol (b) Butan-2-ol (c) 2-methylbutan-2-ol (d) 3-methyl butan-2-ol
Q4 The compound A on treatment with Na gives B, and with PCl5 gives C. B and C react together to
give diethyl ether. A, B and C are respectively
a)C2H5OH, C2H5ONa, C2H5Cl (b) C2H5OH, C2H5Cl, C2H5ONa
(c) C2H5Cl, C2H6, C2H5OH (d) C2H5OH, C2H6, C2H5Cl
Q5 IUPAC name of m-cresol is _______________.
(a) 3-methylphenol (b) 3-chlorophenol (c) 3-methoxyphenol (d) benzene-1, 3-diol
Q6 Mark the correct order of decreasing acid strength of the following compounds

(i)e>d>b>a>c (ii) b>d>a>c> e (iii)d >e>c>b> a (iv) e>d>c>b> a

Q7 The C—O bond length in phenol is less than that in methanol due to
(a) partial = character in aromatic ring (b) sp2 hybridised C (c) sp3 hybridised C (d) both (a) and (b)
Q8 (a) Assertion and Reason both are correct and the Reason is a correct explanation of the Assertion.
(b) Assertion and Reason both are correct but Reason is not a correct explanation of the Assertion.
(c) Assertion is correct but reason is wrong . (d) Assertion is wrong but reason is correct .
Assertion: Aryl halides are not used in the preparation of ethers by Williamson’s synthesis
Reason: Aryl halides undergo elimination reaction in presence of alkoxide.
Q9 Assertion- In Phenol, bromination can take place even in absence of Lewis acid.
Reason- Mono bromination occurs in presence of CHCl3or CS2 at low temperature
Q10 a)Ortho–nitro phenol is more acidic than Ortho–methoxyphenol why?
b) Phenol has small dipole moment than methanol why?
Q11 compound ‘A’ having formula C3H6 ,‘A ‘with aq. H2SO4 give ‘B’ which on treatment with Lucas reagent
gives ‘C’. The compound ‘C’ on treatment with ethanolic KOH gives back ‘A’. Identify A, B, C
Q12 Alcohols are comparatively more soluble in water than the corresponding hydrocarbons why?
Q13 Prove that phenol is o,pdirector
Q14 An organic compound (A) having molecular formula C6H6O gives a characteristic colour with aqueous
FeCl3 solution. (A) on treatment with CO2 and NaOH at 400 K under pressure gives (B), which on
acidification gives a compound (C). The compound (C) reacts with acetyl chloride to give (D) which is a
popular pain killer.identify A,B,C,D
Q15 Give equations of the following reactions: (a) Phenol is treated with conc. HNO3.
(b) Propene is treated with B2H6 , by H2O2/OH– . (c) Sodium t-butoxide is treated with CH3Cl.
Q16 Consumption of Methanol is lethal. Explain why?
Q17 Do Conversion i)Phenol to 2,4,6 Tribromophenol ii)PropenetoPropan -2-ol iii) PropenetoPropanol
Q18 Mechanism for the preparation of ethanolfrom ethene
REVISION ALCOHOLS , PHENOLS, ETHERS L3 HOTS
Q1
Give the IUPAC name of the compound
a)hex-1-en ,2-ol b) hex-2-en ,3-ol c) hex-1-en ,3-ol d) hex-5-en ,4-ol
Q2 Dehydration of alcohol to ethers is catalysed by
(a) cone. H2SO4 at 413 K (b) Hot NaOH at 413 K (c) Hot HBr at 413 K (d) Hot H2SO4 at 443 K
Q3 When Phenol is distilled with Zn dust, it gives (a) Benzene (b) Toluene (c) C6H5CHO (d) Benzoic acid
Q4 Phenol reacts with Br2 in CS2 at low temperature to give
(a) o-Bromophenol (b) o-and p-bromophenols (c) p-Bromophenol (d) 2, 4, 6Tribromophenol
Q5 The correct order of boiling points of alcohol of the same molecular mass :
(a) 1° > 2° > 3° (b) 3° > 2° > 1° (c) 2° > 1° > 3° (d) 2° > 3° > 1°
Q6 Which of the following cannot be made by using Williamson Synthesis:
(a) Methoxybenzene (b) Benzyl p-nitrophenyl ether (c) tert. butyl methyl ether (d) Ditert. butyl ether
Q7 Which is the correct order of acid strength of the following?
(a) C6H5OH > H2O > ROH > HC≡CH (b) C6H5OH > ROH > H2O > HC≡CH
(c) C6H5OH > HC≡CH > H2O > ROH (d) C6H5OH > H2O > HC≡CH > ROH
Q8 A.Assertion and reason both are correct statements and reason is correct explanation for assertion.
B.Assertion and reason both are correct statements but reason is not correct explanation for assertion.
C.Assertion is correct statement but reason is wrong .D.Assertion is wrong but reason is correct.
Assertion: p-hydroxybenzoic acid is more acidic than phenol.
Reason: carboxyl group helps in the stabilisation of theC6H5O- ion by dispersal of negative charge due
to resonance
Q9 Assertion (A) : In lucas test, 3° alcohols react immediately. Reason (R) : An equimolar mixture of
anhyd. ZnCl2 and conc. HCl is called Lucas reagent.
Q1 A compound ‘A’ is optically active. On mild oxidation, it gives a compound ‘B’ but on vigorous
0 oxidation gives another compound ‘C’. C along with D is also formed from B by reaction with iodine
and alkali. Deduce the structures of A, B, C, D
Q1 A compound ‘A’ having molecular formula C4H10O is found to be soluble in concentrated sulphuric
1 acid. It does not react with sodium metal or potassium permanganate. On heating with excess of HI, it
gives a single alkyl halide. Deduce the structure of compound A and explain all the reactions.
Q1 (i) (CH3)3C—OH is treated with Cu at 573 K, (ii) Anisole is treated with CH3Cl/anhydrous AlCl3,
2
Q1 How will you distinguish between butan-1-ol and butan-2-ol?
3
Q1 Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method?
4
Q1 What happens when (a) phenol reacts with bromine water? (b) ethanol reacts with CH3COCl/pyridine?
5 (c) anisole reacts with HI?
Q1 CH2=CHCH2Br + C6 H5 ONa  ?
6
Q1 Why does phenol turn pink after long standing?
7
Q1 Phenol is an acid but does not react with sodium bicarbonate solution. Why?
8
Q1 Mechanism for the preparation of diethyl ether from ethanol
9
Q2 Mechanism for the preparation of Ethene from ethanol
0