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Chapter 15: Q4. (page 570)

Questions: Draw all constitutional isomers formed by monochlorination of each alkane.

a.

b.

c.

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Monochlorination reaction

In the presence of light or heat, alkyl halides are formed by alkanes and halogens. Halogenation is a 鈥渞adical substitution reaction鈥� that occurs via the radical mechanism.

02

 Step 2: Three pathways

The general mechanism for halogenation reaction proceeds through initiation, propagation, and termination.

03

 Step 3: Drawing of constitutional isomers

a. Structure a form only one type of structure because the proton environment is the same. That鈥檚 why all C-H bond cleavages are the same.

Formation of constitutional isomers from a

b. There are three types of halogenation structures because three types of proton can form from 1o and 2o carbon radicals

Formation of constitutional isomers from b

c. In this case, two types of protons can take part in chlorination reactions involving 1o and 2o carbon radicals.


Formation of constitutional isomers from c

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Most popular questions from this chapter

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?

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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?

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Question: a) Draw all constitutional isomers formed by monochlorination of each alkane with Cl2and h谓. (b) Draw the major monobromination product formed by heating each alkane with Br2.
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