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How to evaluate the directing effects of the CH3 group in toluene ?

Macroscale and Microscale Organic Experiments

7th Edition

ISBN:9781305577190

Author:Kenneth L. Williamson, Katherine M. Masters

Publisher:Kenneth L. Williamson, Katherine M. Masters

Chapter20: Bromination And Debromination: Purification Of Cholesterol

Section: Chapter Questions

Problem 4Q

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

How to evaluate the directing effects of the CH₃ group in toluene ?

Expert Solution

Step 1

Toluene is an aromatic hydrocarbon which bears a methyl group (CH₃) attached to the benzene ring. The IUPAC name of toluene is called methylbenzene and its molecular formula is C₇H₈. The presence of methyl group in toluene induces ortho-para directing effect and increases the reactivity of toluene towards electrophilic substitution reactions to form products which are ortho and para isomers.

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