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Chapter 15: Q34. (page 570)

Question: Draw all constitutional isomers formed by monochlorination of each alkane with Cl2 and hv.

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01

Constitutional isomers

The organic compounds with the same molecular formula but different structural arrangements of the constituent elements are known as the constitutional isomers.

02

Monochlorination

The organic reaction involving the replacement of a loosely held hydrogen atom by a chlorine atom initiated by light energy is known as chlorination.

Consider the monochlorination of the given compounds,

a. In 2,2-dimethylhexane five different types of H atom are present that would give five constitutional isomers.


Monochlorination reaction

b. In n-heptane, four different H atom is present that would give rise to four constitutional isomers.


Constitutional isomers

c. In methyl cyclopropane, there are four possible constitutional isomers as follows,


Constitutional isomers of methyl cyclopropane

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Most popular questions from this chapter

Question: Draw the six products (including stereoisomers) formed when A is treated with NBS + hv.

Question: When HBr adds to (CH3)2C=CH2 under radical conditions, two radicals are possible products in the first step of chain propagation. Draw the structure of both radicals and indicate which one is formed. Then draw the preferred product from HBr addition under radical conditions.

Question: The triphenylmethyl radical is an unusual persistent radical present in solution in equilibrium with its dimer. For 70 years the dimer was thought to be hexaphenylethane, but in 1970, NMR data showed it to be A.

a. Why is the triphenylmethyl radical more stable than most other radicals?

b. Use curved arrow notation to show how two triphenylmethyl radicals dimerize to form A.

c. Propose a reason for the formation of A rather than hexaphenylethane.d. How could 1 H and 13C NMR spectroscopy be used to distinguish between hexaphenylethane and A?

Question: Devise a synthesis of CH2 CH2CH2CH2Br from HC≡CH You may use any other required organic or inorganic reagents.

Question: Five isomeric alkanes (A–E) having the molecular formula C6H14 are each treated with Cl2 + hv to give alkyl halides having molecular formula C6H13Cl . A yields five constitutional isomers. B yields four constitutional isomers. C yields two constitutional isomers. D yields three constitutional isomers, two of which possess stereo-genic centres. E yields three constitutional isomers, only one of which possesses a stereo-genic centre. Identify the structures of A–E.
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