Organic chemistry conversions with solutions – Aliphatic compounds.
1. A haloalkane P reacts with aq. KOH to give Q. Q on oxidation with K2Cr2O7/H+ gives R and R under Clemmensen reduction gives S. The compound P react with sodium metal in the presence of dry ether to form 2,3-dimethyl butane. Write the chemical reaction involved and identify P, Q, R and S.
2. An organic compound A reacts with HCN to give B. On hydrolysis of B in an acidic medium, it gives C. Compound A also produces propane when treated with zinc-amalgam and HCl. Identify A, B and C with reaction and give their IUPAC name. What product would you expect when A is treated with trichloromethane in an alkaline medium?
3. An organic compound A on catalytic reduction gives B. B on chlorination gives C, C on heating with sodium metal in the presence of ether gives D, and D on chlorination gives 2-chlorobutane as a major product.
4. A secondary alcohol X reacts with PCl3 to give an alkyl halide Y, which on dehydrohalogenation yields an alkene Z. The alkene Z upon ozonolysis gives a mixture of ethanal and methanal.
5. Consider a reaction:
The compound A is a primary alcohol, which gives the primary iodoform test. Convert the above compound D into ethanoic acid.
6. An organic compound A reacts with PBr3 to give B. Compound B produces C when heated with alc.KOH. The compound C undergoes ozonolysis to yield ethanal and methanal as major products. The compound A responds to the iodoform test. How is A obtained from CH3MgBr?
Propan-2-ol can be obtained from CH3MgBr as follow:
7. How is ethanol prepared from
i. ethyne?
ii. 1-1 dichloroethane?
iii. Convert ethanol into propanone.
i. From ethyne:
ii. From 1-1 dichloroethane:
iii. Converting ethanol to propanone:
8. Consider the following reaction:
The compound A is a primary alcohol, which on oxidation gives ethanal. Convert A into methanol and ethyne.
Converting A into methanol and ethyne:
9. Convert the following:
i. propan-2-ol into propan-1-ol.
ii. Propan-1-ol into propan-2-ol
iii. Ethanol into propan-1-ol
iv. Propanone into ethanol
v. Chloroform to dimethyl amine
vi. Methoxy ethane to ethoxy ethane
vii. Ethoxyethane to methoxy ethane
viii. Ethanol to methoxy ethane
ix. Ethoxy ethane to ethanoyl chloride
x. Ethanal to 3-hydroxy butanal (aldol)
xi. Propanone to 2-hydroxy 2-methyl propanoic acid
xii. Propanone into 4-hydroxy 4-methyl pentan-2-one
xiii. Ethanal to 2-hydroxy propanoic acid
