The conversion of 2 − methyl − 2 − butene into 2 − methyl − 1 , 3 − butadiene and ethylbenzene into 3 − phenylacrylonitrile and the product of the Diels Alder reaction is to be determined. Concept introduction: ▸ The reagent NBS is used for the allylic bromination of the alkene and the mechanism of the reaction involves the formation of free radicals. ▸ The dehydrohalogenation of halo alkene takes place in the presence of a base like KOH to form the alkene as a product. ▸ The process in which the alkene is treated with ammonia and oxygen for the formation of nitrile is known as Ammoxidation. ▸ A reaction in which dienes and dienophiles react with each other to form the cyclic compound is known as Diels Alder reaction.

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Chapter 13, Problem 2LGP

Interpretation Introduction

Interpretation:

The conversion of 2−methyl−2−butene into 2−methyl−1,3−butadiene and ethylbenzene into 3−phenylacrylonitrile and the product of the Diels Alder reaction is to be determined.

Concept introduction:

▸ The reagent NBS is used for the allylic bromination of the alkene and the mechanism of the reaction involves the formation of free radicals.

▸ The dehydrohalogenation of halo alkene takes place in the presence of a base like KOH to form the alkene as a product.

▸ The process in which the alkene is treated with ammonia and oxygen for the formation of nitrile is known as Ammoxidation.

▸ A reaction in which dienes and dienophiles react with each other to form the cyclic compound is known as Diels Alder reaction.

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1)Chemistry students are taking an experimental course in organic chemistry at a public university. During an experiment involving conjugated dienes, some doubts arose when discussing the results obtained so far: (a) A student obtained two products from the reaction of 1,3-cyclohexadiene with Br2. His lab partner was surprised to get only one product from the reaction of 1,3 - cyclohexadiene with HBr. Explain these distinct results. (b) One student, seeing the discussion of colleagues, commented that she obtained two distinct products when reacting 1,3,5-hexatriene with HBr, with different yields just by changing the reaction temperature. Explain the results she obtained using reaction mechanism and based on kinetic and thermodynamic control involving conjugated dienes.

(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation. (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active. (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C. (iii) Name the product formed when compound A undergoes bromination reaction.

Explain why (i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride. (ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.