Alcohol , Phenol and Ether(By: Jitender sir)

Questions
1. In esterification if we have used acid chloride instead of acid anhydride then we add pyridine a base. Why?
2. (a) What is the limitation of Williamson`s synthesis?
(b) Why sec. and tert. Alkyl haides undergo elimination process in Williamson`s synthesis?
3. Explain why is ortho nitrophenol more acidic than ortho methoxyphenol.
4. Write the structures of the major products expected from the following reactions:
(a) Mononitration of 3-Methylphenol (b) Dinitration of 3-Methylphenol
(c) Mononitration of phenyl Ethanoate.
5. The following is not an appropriate reaction for the preparation of t-butyl ethyl ether.
CH3 CH3

H3C C Cl + H3C CH2 O Na H3C C O CH2 CH3

CH3 CH3

2-chloro-2-methylpropane 2-Ethoxy-2-methylpropane
(i) What would be the major product of this reaction?
(ii) Write a suitable reaction for the preparation of t-butyl ethyl ether.
6. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give
reason.
7. Convert the following:
(i) Ethanol to Ethoxy ethane
(ii) Prop-1-ene to propan-1-ol
(iii) Methanal to benzyl alcohol
(iv) Ethanol to Butan-2-ol
(v) Methyl magnesium bromine to 2-Methylpropan-2-ol
(vi) Phenol to Aspirin(Acetoxy benzoic acid)
8. An organic compound A (C2H6O) react with sodium to form a compound B with the evolution of H2 and gives
a yellow compound C when treated with iodine and NaOH. When (A) heated with conc. H2SO4 at 413K, it
gives a compound D ( C4H10O) which on treatment with conc. HI at 373K gives E and A. D is also obtained
when B is heated with E. Identify A, B,C, D and E and write equations for the reactions involved.
9. What happen when Phenol is treated with-
(a) Br2/ CS2
(b) Bromine water
(c) Dilute HNO3
(d) Conc. HNO3
10. Explain the mechanism of the following :
(i) Hydration of alkene (ii) Dehydration of ethanol at 443K
11. A compound C3H8O ( A) on dehydrogenation by Cu/573K give a compound C3H6O(B) which on reaction with
suitable Grignard reagent (C) to give compound (D) which on treatment with Cu / 573K gives an alkene (E) with
a molecular formula C4H8. Find out A ,B,C, D and E.
12. Arrange the following compounds in increasing order of boiling point. Propan-l-ol, butan-2-ol, pentan-l-ol.
13. How can you distinguish between phenol and benzyl alcohol?
14. Explain why nucleophilic substitution reactions are not very common in phenols.
15. Out of benzene and phenol, which one is more easily nitrated and why?
16. Explain the following reaction: (i) Reimer Tiemann reaction (ii) Kolbe reaction.
17. What happen when phenol is treated with (i) Acetyl chloride/Anhyd. AlCl3 (ii) Conc. HNO3
18. Why is the C – O – H bond angle‘in alcohols slightly less than the tetrahedral angle whereas the C – O – C
bond angle in ether is slightly greater?
19. Phenol is a very weak acid. What substitution in the molecule can make it a stronger acid and a weaker
acid & why?
20. Which are the suitable reagent for the following reaction:
(i) Propa-2-ol to propene (ii) 3o Alcohol to alkene (iii) Ethanol to Ethoxyethane
21. Why is phenol more acidic than an alcohol?
22. Now a days which new method we are applying for formation of picric acid?
23. How can you convert phenol to p-Benzoquinone?
24. Why C-O bond length in phenol is shorter then alcohol?
25. Out of o-Nitrophenol and p-Nitrophenol which is more steam volatile?
26. Give the products:
CH3
HI
(i) H3C CH2 CH CH2 O CH2 CH3
heat
CH3
HI
(ii) H3C CH2 CH2 O C CH3
heat
CH3
27. Which of the following is an appropriate set of reactants for the preparation of 1-methoxy-4- nitrobenzene
and why?
Br

(i) + CH3ONa

NO2

ONa
(ii)
+ CH3Br

NO2

28. Fill in the blank and find out the A, B, C ,D and E ?

H+ /H O
Cu/573K CH MgBr
Na metal 3 2
CH CH −Br
(i) CH2 = CH − CH3 ⎯⎯⎯⎯⎯
2 → A ⎯⎯⎯⎯⎯ → B ⎯⎯⎯⎯⎯
+
3 → C ⎯⎯⎯⎯⎯ → D ⎯⎯⎯⎯⎯⎯→
williamson`s
E
H /H2O

CH −Mg−Br Conc.H SO Na Metal H+ /H O SOC

(ii) A ⎯⎯⎯⎯⎯⎯
3
+ ⎯
→ B ⎯⎯⎯⎯⎯⎯
2 4 → CH = CH ⎯⎯⎯⎯⎯
443K 2 2
2 → C ⎯⎯⎯⎯
2 → D ⎯⎯⎯⎯⎯
Dry ether
→E
H /H2O

CH=CH2 H+/H2O (A) How we will get same compound (A) with Ethanal(CH3CHO)
(iii) B2 H /
6 OH
(B) How we will get the same product (B) with methanal(HCHO)
 CH3 B2H6 / H2O2
20% H3PO4 / 358K
(iv) CH3 - C -OH (B) (C)
OH- / H2O
CH3

CH3-CHCH LiAlH4
2(OH)CHCH
-CH2OH2CH3
3
(A) (E)
Pentain-2-ol

(J)

H+ / H2O
CH33-CH
CH -CH22-OH
-OH CH2=CH2
(B) (K) (L)
Ethanal
( 1oAlcohol)

CH3 85% H3PO4

CH3-Mg-X (M)
(C) CH3-CH-OH 440K
Propan-2-ol
(2oalcohol)

(P)
O
CH3-C-CH3 Cu/573K
(N)

(D)

H+/H2O

Q1. An alcohol A (C4H10O) on oxidation with acidified potassium dichromate gives carboxylic acid B
(C4H8O2). Compound A when dehydrated with Conc. H2SO4 at 443 K gives compound C. Treatment of C with
aqueous H2SO4 gives compound D (C4H10O), which is an isomer of A. Compound D is resistant to oxidation,
but compound A can be easily oxidised. Identify A, B, C, D and write their structures.
Best of luck: Jitender sir