ALCOHOLS, ETHERS & PHENOLS
Very short answer type questions
Q.1. What product are obtained when 
is treated with HI?
Q.2. Why a non-symmetrical ether is not prepared by heating a mixture of ROH and R’OH in acid?
Q.3. Write IUPAC name of the compounds;
Q.4. Name the reagents used in oxidation of a Primary alcohol to carboxylic acid.
Q.5. Sodium metal can he used for drying diethyl ether but not ethanol. Why?
Q.6. Name the pair of alkyl halide and alkoxide for the preparation of ethyl-tert butyl ether.
Q.7. Boiling point of glycol is high. Why?
Q.8. Arrange the following in the decreasing order of their boiling points :
CH3 CH2 OH, HOCH2 CH2 OH, CH3 CH2 Cl
Q.9. Can we dry ethanol by anhydrous CaCl2?
Q.10. Arrange the following compounds in increasing order of their acid strength :
Propan -1-ol; 2, 4, 6 – trinitrophenol; nitrophenol; 3, 5 – dinitrophenol phenol; 4 – methyl phenol
Q.11. Phenol are more acidic than alcohols. Why?
Q.12. Write the equations for the preparation of propan-2-ol from Propene
Q.13. Give chemical test to distinguish between 1-nitropropane 2 and nitropropane.
Q.14. How would you convert propanone to iodoform?
Q.15. Which electrophile is involved in the nitration of benzene?
Short answer type questions
Q.1. How are the following conversions carried out ? (Write the reactions and condition in each case) :
(i) Ethanol to 2-propanol (ii) Phenol to Acetophenone
Q.2. (a) Give chemical tests to distinguish between the following pairs of compounds
(i) Propanoyl chloride and Propanoic acid
(ii) Benzaldehyde and Acetophenone
(b) Write IUPAC name of CH3 – CH2CONH. C6H5.
Q.3. Explain why alcohols arc comparatively more soluble in water than the corresponding hydrocarbon.
Q.4. How is t-butyl alcohol obtained from acetone ?
Q.5. Why has phenol higher boiling point than toluene?
Q.6. While separating a mixture of ortho and para nitrophenol by steam distillation, name the isomer which is more volatile. Give reason.
Q.7. Explain why orthonitrophenol is more acidic than orthomethoxy phenol.
Q.8. How will you convert propan -1-ol to propan -2- ol?
Q.9. Ethers possess a dipole moment even if the alkyl radicals in the molecule are identical. Explain?
Q.10. How does anisole reacts with Br, in CS2?
Q.11. How do you account for the miscibility of ethoxyethane with water?
Q.12. Classify the following as primary and secondary alcohols;
(i) H2C = CH – CH2OH (ii) 
Q.13. Give the equation of reaction for the preparation of phenol from cumene
Q.14. You are given benzene, conc. H2SO4 and NaOH. Write the equation for the preparation of phenol using these reagents.
Long answer type question
Q.1. Write the chemical reaction equation stating the reaction condition required for each of the following conversion.
(i) Methyl bromide to ethylamine
(ii) Aniline to phenol
(iii) p-toluidine to 2-bromo-4-methylamine
Q.2. Answer the following giving reaction condition and a complete chemical equation in each case:
(i) How would you prepare ethyl amine from acetaldehyde?
(ii) How can you get benzonitrile from aniline?
(iii) How is ethyl carbylamine obtained from ethyl amine?
Q.3. Give chemical tests to distinguish between the following pairs of compound:
(i) Propanal and propanone (ii) Methyl acetate and ethyl acetate
(iii) Benzaldehyde and benzoic acid
Q.4. (a) Explain the following observation:
(i) Primary amines have higher boiling than comparable tertiary amine.
(b) Mention two important uses of N, N- Dimethyl aniline (DMA).
Q.5. How would you bring about the following conversions:
(i) Propanal to butanone (ii) Benzaldehyde to benzophenone
(iii) Benzoyl chloride to benzonitrile?
Give the complete chemical equation and reaction conditions in each case.
Q.6. Give the equation for the following reactions:
(a) Reaction of bromine in CS2 with phenol. (b) Reaction of dil. HNO3, with phenol.
(c) Treating phenol with chloroform in the presence of aquous KOH at 343 K.
Q.7. How would you convert
(a) Benzoic acid to benzamide (b) Methanol to ethanol
(c) Ethanol to acetone.
Q.8. (a) Arrange HClO3, HClO2, HOCl and HClO4 in order of increasing acid strength. Give reason for your answer.
(b) Write the balanced chemical equation for the reaction of Cl2 with hot and conc. NaOH solution. Justify that this reaction is a disproportionation reaction.
(c) Give one use of ClF3.
Q.9. (a) Name the reagents and write the chemical equations for the preparation of the following compounds by Williamson’s synthesis:
(i) Ethoxybenzene (ii) 2-Methyl-2-methoxypropane
(b) Why do phenol not give the Protonation reaction readily?
Q.10. What happens when D-glucose is treated with the following reagents?
(i) HI (ii) Bromine water (iii) HNO3
Very long answer type questions
Q.1. (a) How will you bring about the following conversions?
(i) Benzene to acetophenone
(ii) Benzoic acid to benzaldehyde
(b) Describe the following giving a suitable example in each case:
(i) Decarboxylation
Q.2. (a) How will you convert
(i) Benzoyl chloride to benzaldehyde (ii) Propanone to 2-propanol
(iii) Benzoic acid to m-nitrobenzoic acid
Write the reaction and dale the reaction conditions in each case.
(b) Write the names and structures of the products formed in the following reactions:
(i) Reaction of semicarbazide (NH2 CONHNH2) with formaldehyde
(ii) Oxidation of ethyl benzene with alkaline KMnO4
Q.3. Write the structures of the reagents/ organic compounds A to E in the following sequence of reactions:
Q.4. An organic A (C3H6O) is resistant to oxidation but forms compound B (C3H8O) on reduction. B reacts with HBr to form the compound C. C with Mg forms Grignard reagent D which reacts with A to form a product which on hydrolysis gives E. Identify A to E.
Q.5. (a) Draw the structure and write the hybridisation state of Co in cis – [Co(NH3)4 Cl2]+.
(b) Using the IUPAC norms name the following complex:
[Co(NH3)4 Cl (ONO)] Cl
(c) What happens when white phosphorus is heated with cone. NaOH solution in an inert gas atmosphere?
