COMPETENCY BASED QUESTIONS

1. 896 ml of a hydrocarbon (A) having 87.80% C and 12.19% H weights 3.28

g at STP. Hydrogenation of (A) gives 2-methylpentane. Also compound (A)
on hydration in presence of H2SO4 and HgSO4 gives Ketone (B) having
molecular formula C6H12O. The ketone (B) gives a positive iodoform test.
Find the structure of (A) give all reactions.
[Hint : (i) 1 mole of a compound at STP contains 22400 mL volume
(ii) Ketones having structures gives positive iodoform test]
2. Explain why the central carbon-carbon bond in 1,3-Butadiene is shorter than
that of butane.
3. How do you explain that dehydration of 3,3-Dimethyl, butan-2-ol yield 2,3
Dimethyl but-2-ene as the major product.[Hint: Rearrangement of 1,2
methyl shift]
4. In alkyl halide X of molecular formula C6H13Cl, on treatment with
potassium tertiary butoxide gives two isomeric alkenes, Y and Z.(C6H12)
Both alkene on hydrogenation give 2,3 dimethyl butane. Predict the
structures of X,Y and Z.
5. Two cyclic dienes, A and B have M.F C6H8. The mixture of the two on
reductive ozonolysis gave the following products: Succinaldehyde, Propan
1,3 dial, and glyoxal. The mixture of A and B on hydrogenation produces
only cyclohexane. Suggest the structures of A and B.
6. Arrange the following compounds in the order of their decreasing relative
reactivity with an electrophile.
a) Toluene, 4-nitro toluene. 1,4-DinitroBenzene
b) Chlorobenzene, p-Nitro chlorobenzene, 2,4-Dinitro chlorobenzene
7. What effect does branching of an alkane chain has on its melting point than
that of its long chain isomers? Explain.
8. In the presence of peroxide addition of HBr to propene takes place according
to anti Markonikov’s rule, but peroxide effect is not seen in the case of HCl
and HI. Explain.
9. An alkane C8H18 is obtained as the only product on subjecting a primary
alkyl halide to Wurtz reaction. On monobromination this alkane yields a
single isomer of a tertiary bromide. Write the structure alkane and the
tertiary bromide.
10. Write down a method of preparation of Nitrobenzene from Acetylene.