Important questions(Alcohols,Phenols and Ethers.
Aldehydes,Ketones and Acids)
Alcohols phenols and ethers
1. An ether A (C5H12O) when heated with excess of hot concentrated HI produced two alkyl halides which on
hydrolysis from compounds B and C. Oxidation of B gives an acid D whereas oxidation of C gave a ketone E.
Deduce the structure of A,B C,D and E.
2. An alcohol A (C4H10O) on oxidation with acidified K2Cr2O7 gives carboxylic acid B (C4H8O2). Compound
A when dehydrated with conc. H2SO4 at 443 K gives compound ‘C’ with aqueous H2SO4 C’ gives
compound ‘D’ (C4H10O) which is an isomer of ‘A’. Compound ‘D’ is resistant to oxidation but
compound ‘A’ can be easily oxidized. Identify A, B, C and D.
Ans : A : (CH3)2CHCH2OH B : CH3CH(CH3)COOH
C : (CH3)2C = CH2 D : (CH3)3 – C – OH
3. Phenol C6H5OH when it first reacts with concentrated sulphuric acid forms Y. the compound Y is reacted
with concentrated nitric acid to form Z. Identify Y and Z and explain why phenol is not converted
commercially to Zn by reacting it with Con, HNO3.
4. How will you convert :
a. Phenol to cyclohexanol
b. Benzyl chloride to benzyl alcohol.
c. Anisole to phenol.
5. Give equations of the following reactions :
a. Oxidation of propan-1-ol with alkaline KMnO4 solution.
b. Bromine in CS2 with phenol.
c. Treating phenol with chloroform in presence of aqueous NaOH.
6. Account for the following :
a. Phenol has a smaller dipole moment than methanol.
b. Phenol goes electrophilic substitution reaction.
Ans: a. Due to – ve charge on oxygen in delocalized by resonance.
b. Due to greater electron density than benzene.
7. Complete the following equations and name the products :
8. Ethereal solution of an organic compound ‘X’ when heated with Mg gave Y. Y’ on treatment
with CH3CHO followed by acid hydrolysis gave 2-propanol. Identify the compound ‘X’. What is
‘Y’ known as?
9. Write the reactions and conditions involved in the conversion of :
a. Propene to propan-2-ol.
b. Phenol to salicylic acid.
10. Arrange in order of boiling points :
a. C2H5 – O – C2H5, C4H9COOH, C4H9OH
b. C3H7CHO, CH3COC2H5, C2H5COOCH3, (CH3CO)2O
Ans: C4H9COOH > C4H9OH > C2H5 – O – C2H5
(CH3CO)2O > C2H5COOCH3 > CH3COC2H5 > C3H7CHO
11. An organic compound X has molecular formula C5H10O. It does not reduce Fehling’s solution
but forms a bisulphite compound. It also gives positive Iodoform test. What are possible
structures of X? Explain your reasoning relating structure.
Ans: Ketone give +ve test with Iodoform. It is methyl Ketone.
12. Give the chemical test to distinguish between ;
a. CH3CHO AND CH3COCH3
b. CH3CHO AND C6H5CHO
(a) CH3CHO gives Tollen’s reagent test.
CH3CHO + 2AgNO3 + 2NH4OH → CH3COOH + 2Ag + 2NH4NO3 + 2H2O
Silver mirror
(b) CH3CHO gives brick red ppt.
CH3CHO + 2CuSO4 + 4NaOH → CH3COOH + Cu2O + Na2SO4 + 2H2O
Brown red ppt.
13. Complete the following reactions by identifying A, B and C
14. Do the following conversions in not more than two steps :
a. Benzoic acid to Benzalolehyde
b. Propanone to propene
15. Convert the following (i) Ethyl benzene to benzoic acid (ii) Ethanal to but-2-enal.
16. Predict the organic products of the following reactions :
Ans ;
17. Write chemical reaction to affect the following transformations :
18. Give reasons for the following:
a. Carboxylic acids do not give characteristic reactions of carbonyl group
b. Treatment of C6H5CHO with HCN gives a mixture of two isomers which cannot be
separated even by fractional distillation.
c. Sodium bisulphite is used for purification of ketones and aldehydes.
19. Write the structures of A, B, C, D and E in the following reactions:
Ans : A = CH5COCH3 B = C6H5CH2CH3
C = C6H5COOH
D = C6H5COONa
E = CHI3