1. Predict whether the following compound is likely to be aromatic. Explain why.

2. Identify any basic nitrogen atoms in the structure.

Copper iodide (CuI) precipitates when 3-iodocycloprop-1-ene is treated with copper tetrafluoroborate (CuBF₄). The organic product formed can be obtained as a solid substance that dissolves readily in polar solvents like ethanol but does not dissolve in non-polar solvents like hexane. 3-iodocycloprop-1-ene gets regenerated when this solid substance is dissolved in ethanol containing potassium iodide (KI). Provide the structure of this solid substance and write down equations for its formation and reaction.

What major product is expected from the coupling reaction shown below?

Determine the products of the coupling reactions below:

Write a mechanism for the reaction of toluene with bromine in the presence of FeBr₃ as a catalyst.

Prior to the advent of modern spectroscopic techniques, Körner’s approach was employed to distinguish between the ortho, meta, and para isomers of disubstituted benzene derivatives. This method involves introducing a third substituent group (commonly a nitro group) and determining the number of isomeric products formed. For instance, when catechol undergoes nitration, two distinct isomers are obtained:

How many isomeric products would be formed in the nitration of hydroquinone?

Draw the major product for the reaction of benzene with the given reagents below.

(i) 2-bromo-2-methylbutane, AlCl₃

(ii) 1-chloropropane, AlCl₃

Using Friedel–Crafts acylation reaction, propose the synthesis of propylbenzene.

I. What are the products of the electrophilic aromatic substitution reaction of benzene and the given epoxide in the presence of a Lewis acid such as AlCl₃?

II. Do you think aziridines will react similarly?

Arrange the following substituted benzenes in decreasing order of reactivity in an electrophilic aromatic substitution reaction.

Show how you would accomplish the synthesis shown below.

A student tried to produce 3-propylbenzenesulfonic acid from benzenesulfonic acid and 1-chloropropane through the Friedel-Crafts alkylation.
Is this a feasible reaction to get the desired compound? If not, suggest an alternative synthesis.

Unlike other electrophilic aromatic substitutions, benzene sulfonation is reversible. Sulfonic acid can be added to the benzene ring and removed later. This makes the sulfonic acid group alternatively known as the "blocking group." Show how to synthesize 1,2,3-tribromobenzene starting from benzene, using sulfonation and de-sulfonation as intermediate steps.

Chlorobenzene is more reactive towards electrophilic aromatic substitution than bromobenzene. However, (bromomethyl)benzene is more reactive than (chloromethyl)benzene. Rationalize this observation.

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.

Give the product of the reaction given below:

Propose the plausible structure of the product and the mechanism of its formation.

Write the correct synthetic sequence for preparation of the following compound using Friedel–Crafts acylation and/or Clemmensen reduction.

The compound below is involved in the synthesis of proxymetacaine. Show how to synthesize the compound from phenol.

Provide the product formed from the reaction shown below.

Draw the plausible product of the reaction between p-chloroaniline and benzenediazonium chloride.

Determine the amide bond in the following compound that is hydrolyzed in the first step when it is converted to methyldiazonium.

Provide the mechanism for the reaction below:

The last step in the reaction below is a Diels-Alder reaction. Propose a plausible mechanism for the formation of the dienophile in the reaction.

Name the carbonyl-containing compound below. If possible, provide both common and IUPAC names.

CH₂(Cl)CH₂CH₂CH₂CH(CH₃)CHO

Draw the molecular orbitals to show the bonding in propan-2-one.

Propose the reagent(s) needed to accomplish the following synthesis efficiently and in good yield.