Side-Chain Halogenation - Online Tutor, Practice Problems & Exam Prep

Draw the mechanism for the following reaction.

Propose the products formed by the light-induced reaction of the following compounds with (i) 1 equivalent of bromine and (ii) excess of bromine.

a. Toluene
b.

What would be the major product formed in the given reaction?

Draw the major product formed in the benzylic bromination reaction shown below.

Show how ethylbenzene can be converted to the product shown below using a single-step reaction.

Commercial supplies of the solvent tetrahydrofuran (THF) are often stabilized with a small amount of BHT to prevent autoxidation upon exposure to air. Draw the mechanism that shows how BHT intercepts autoxidation. Assume that the initiation step is caused by a generic R radical.

The following reaction intended to make molecule (i) but formed molecule (ii) instead. Draw the mechanism for the formation of molecule (ii).

The following reaction intended to make molecule (i) but formed molecule (ii) instead. Which marked C-H bond is expected to have a lower bond-dissociation energy?

A radical reaction involves the following radical species in its propagation steps. Draw the 6 possible products from the termination steps.

True or False: In the second propagation step in the bromination of toluene, the bromine molecule is more likely to add to the aromatic ring than to the benzyl position due to the stability of the benzyl radical.

Show the major products of free-radical bromination of the given compound below. Keeping in mind that bromination is highly selective towards the stable radical formation.

iso-Propyl benzene

Predict the product of the addition of HBr to but-1-en-1-ylbenzene in the presence of a free-radical initiator. Show the mechanism (initiation and propagation) for the reaction.

Determine the reagents and conditions necessary for the reaction that would produce the following bromoalkane.

Draw the product(s) formed in the benzylic bromination reaction shown below.

Draw the major product of the reaction given below. Do not include stereoisomers.

Which of the following compounds is produced as a result of the benzylic bromination reaction?

Provide a reaction scheme showing the conversion of butylbenzene to (1-bromobutyl)benzene. Explain the possible unwanted reactions that could result in undesirable impurities in the product.

Draw the products of the light-initiated reaction of NBS with the following compound.

What are the major oxidation products expected when the following compounds are treated with hot basic KMnO₄, and then acidified with HCl (dilute)?
a. toluene
b.

c. o-xylene