1. Write the equations of the following named reactions:
a) Hydro boration
b) williamson's synthesis
c) cumene phenol process
d) Kolbe's reaction
e) Riemier Tiemann reaction
2. Explain Lucas test with suitable examples
3. Distinguish chemically between the following pairs of organic compounds
a) Phenol and methanol
b) methanol and ethanol
c) propan-1-ol and propan-2-ol
d) pentan-3-ol and 2-Methyl butan 2-ol
4. Account for the following:
a) COH bond angle in alcohol is less than tetrahedral angle of 109.50
b) COC bond angle in ether is more than tetrahedral angle of 109.50
c) C-O bond length in phenol is less than that of alcohol.
d) Phenol has lower dipole moment than alcohol.
e) Phenol under goes electrophillic substitution at ortho and para position
f) Alcohol acts as a bronsted acid as well as bronsted base.
g) Phenol is more acidic than alcohol.
h) Acidity of alcohol is primary alcohol>sec alcohol>tert alcohol.
i) Basicity of alcohol is tert alcohol> sec alcohol>primary alcohol.
j) In Williamson’s synthesis sec and tert halide can not be used.
k) para nitro phenol is less steam volatile than ortho nitro phenol.
l) Presence of nitro group at ortho and para position makes phenol more acidic.
m) Alcohols and phenols have higher boiling point.
n) Boiling point of alcohol is higher than its isomeric ether.
o) Boiling point of glycerol>ethylene glycol> ethanol.
p) Grignard reagent is a versatile reagent in organic chemistry.
q) Cresol is less acidic than phenol.
r) In esterification reaction, water is removed as soon as it is formed.
s) Order of reactivity of HX with alcohol is HI>HBr>HCl>HF
t) Alcohol reacts with SOCl2 to give pure halo alkane.
u) Ease of dehydration of alcohol is tert alcohol> sec alcohol>primary alcohol.
v) Phenol and anisole undergoes bromination reaction even in the absence of halogen carrier.
w) Methyl phenyl ether reacts with HI to give phenol and methyl iodide and not methanol and iodo benzene.
x) Methoxy ethane reacts with HI to give methyl iodide and ethanol and not ethyl iodide and methanol.
y) Tert butyl methyl ether reacts with HI to give tert butyl iodide and methanol and not not methyl iodide and tert butyl alcohol.
z) Anisole undergoes electrophillic substitution at ortho and para position.
aa) Boiling point of butan-1-ol is higher than tert butyl alcohol.
bb) Alcohol, phenol and ether are soluble in water.
cc) In the reaction between acid chloride and alcohol a small amount of pyridine is added.
dd) Alcohol behaves as nucleophile as well as electrophile.
ee) Water is a stronger acid than alcohol.
5. Carry out the following conversions:
a) Ethanal to ethanol.
b) Acetone to propan-2-ol.
c) Ethanoic acid to ethanol.
d) Ethene to ethanol.
e) Propene to propan-2-ol.
f) Methanal to ethanol.
g) Methanal to benzyl alcohol.
h) Ethanal to propan-2-ol.
i) Acetone to 2-methyl propan-2-ol.
j) But-1-ene to butan-1-ol.
k) But-2-ene to butan-2-ol.
l) Chloro benzene to phenol.
m) Aniline to phenol.
n) Benzene to phenol.
o) Ethanol to ethyl ethanoate.
p) Ethanol to ethene.
q) Ethanol to ethanal.
r) Tert butyl alcohol to 2-methyl prop-1-ene.
s) Propan-2-ol to acetone.
t) Phenol to
i) phenyl ethanoate.
ii) 2-Acetoxy benzoic acid.
iii) ortho and para nitro phenol.
iv) 2,4,6-trinitro phenol
v) para bromo phenol
vi) 2,4,6- tri bromo phenol
vii) salicylic acid
vii) salicylaldehyde
viii) anisole
ix) phenatole
x) benzene
xi) benzo quinone.
u) Ethyl iodide to diethyl ether
v) Methyl bromide to 2 methoxy 2 methyl propane.
w) Benzyl chloride to benzyl alcohol
x) Ethyl magnesium chloride to propan-1-ol
y) Cumene to phenol
z) Anisole to
i) phenol
ii) ortho and para hydroxyl aceto phenone
iii) para bromo anisole
iv) ortho and para methyl anisole
v) ortho and para methoxy aceto phenone
vi) ortho and para nitro anisole
vii) Ethene to ethane-1,2-diol
6. Explain the mechanism of the following reactions:
a) CH2= CH2 + H2O 
CH3CH2OH
b) CH3CH2OH CH2= CH2 + H2O
443K
413K
c) CH3CH2OH CH3CH2OCH2CH3
d) Explain the mechanisms of the reactions in which alcohol acts as
a) nucleophile
b) electrophile
7. How is ethanol prepared from
a) ethene
b) cane sugar? Mention 2 uses of ethanol.
8. How is methanol commercially? Mention 2 uses of the same.
9. How is phenol prepared commercially? Mention 2 uses of the same.
10. An organic compound A react with NaOH under drastic condition to give B. B reacts with
Br2(aq) to give C.C on zinc dust distillation gives 1,3,5-Tribromo benzene. Identify the compounds and write the equations of the reactions involved.
11. Give the mechanism for the reactio
(CH3)2CH-CH3 (CH3)2C-CH3
| HBr |
OH Br
12. Write the equations of the following reactions:
a) Friedel-Craft’s alkylation of anisole.
b) Friedel-Craft’s acylation of anisole.
c) Nitration of anisole.
d) Bromination of anisole in ethanoic acid medium.
e) Oxidation of Propan-1-ol with alkaline KMnO4 solution
f) Phenol with Br2 in CS2
g) Phenol with dilute HNO3
h) Phenol with chloroform in the presence of aqueous NaOH.
13. Write the equation of reaction of HI with
a) 1-Propoxy propane
b) Methoxy benzene
c) benzyl ethyl ether.
d) CH3-CH2-CH(CH3)-CH2OCH2-CH3
e) C6H5CH2OC6H5
CH3
|
f) CH3-CH2-CH2-O-C-C2H5
|
CH3
14. Name the reagent used in the following reactions:
a) Oxidation of primary alcohol to carboxylic acid.
b) Oxidation of primary alcohol to aldehyde.
c) Bromination of phenol to 2,4,6-Tribromophenol.
d) Benzyl alcohol to benzoic acid.
e) Dehydration of Propan-2-ol to propene.
f) Butan-2-one to Butan-2-ol.
15. You are given benzene, concentrated sulphuric acid and NaOH. Write the equation
involved in the preparation of phenol using these reagents.
16. Give the products of the following reactions:
a) CH3-CH2-CH2-OCH3 +HBr
b) C6H5OC2H5 +HBr
c) (CH3)3COC2H5 +HI
d) C6H5OC2H 5
conc HNO3+conc H2SO4
e) CH3CH=CH2
H3O+
f) CH3-CH2-CH-CHO
| NaBH4
CH3
g) 
17.�Give the structure and IUPAC names of the products expected from the following reactions:
a) Catalytic reduction of butanal
b) Hydration of propene in the presence of dilute sulphuric acid.
c)�Reaction of propanone with methyl magnesium bromide followed by hydrolysis.
18.�The following is not the appropriate reaction for the preparation of tert-butyl ethyl ether.
C2H5ONa+(CH3)3C-Cl (CH3)3COC2H5
a)�What would be the major product for this reaction ?
b)�Write the reaction for the preparation of tert-butyl ethyl ether.
19.�Give the structure of the product you would expect when each of the following alcohol react with
�i) HBr
�ii) SOCl2�
iii) ZnCl2+HCl
a) Butan-1-ol
b) 2-Methylbutan-2-ol
20.�Predict the major product in the acid catalysed dehydration of
a) butan-1-ol�
b) 1-Methylcyclohexanol.
21.�Draw the resonance structures of phenoxide ion of ortho and para nitrophenols.
22.�Write the structure of major products formed in the following reactions:
a) Mono nitration of 3-methylphenol.
b) Dinitration of 3-methylphenol.
c)�Mononitration of phenyl methanoate.
23. How are the following alcohols prepared by the reaction of Grignard reagent with HCHO?
a) (CH3)2CHCH2OH
b) CH2OH
|
24. Arrange the following compounds in the order of properties mentioned:
a) Pentan-1-ol, Pentan-2-ol, ethanol, Propan-1-ol and methanol.(increasing order of boiling point.
b) Pentan-1-ol, n-butane, Pentanal and ethoxyethane.(increasing order of boiling point.)
c) Propan-1-ol, 2,4,6-Trinitrophenol, 3-Nitrophenol, 3,5-Dinitrophenol, Phenol and
4-Methylphenol( increasing order of acidity)
