Give structures for the products of each of the following...

Give structures for the products of each of the following reactions: (a)(FIGURE CANNOT COPY) (b)(FIGURE CANNOT COPY) (c)(FIGURE CANNOT COPY) (d)(FIGURE CANNOT COPY) (e)(FIGURE CANNOT COPY) (f)(FIGURE CANNOT COPY) (g) Aniline + propanoyl chloride $\longrightarrow$ (h) Tetraethylammonium hydroxide $\frac{1}{\text { heat }}$ (i) $p$ -Toluidine $+\mathrm{Br}_{2}$ (excess) $\overrightarrow{\mathrm{H}_{2} \mathrm{O}}$

Give structures for the products of each of the following reactions:
(a)(FIGURE CANNOT COPY)
(b)(FIGURE CANNOT COPY)
(c)(FIGURE CANNOT COPY)
(d)(FIGURE CANNOT COPY)
(e)(FIGURE CANNOT COPY)
(f)(FIGURE CANNOT COPY)
(g) Aniline + propanoyl chloride $\longrightarrow$
(h) Tetraethylammonium hydroxide $\frac{1}{\text { heat }}$
(i) $p$ -Toluidine $+\mathrm{Br}_{2}$ (excess) $\overrightarrow{\mathrm{H}_{2} \mathrm{O}}$

Key Concepts

Directing Effects in Aromatic Substitution

Substituents already present on an aromatic ring affect both the rate and the orientation of further electrophilic aromatic substitutions. Activating groups (such as an amino group) generally direct incoming electrophiles to the ortho and para positions, whereas deactivating groups (or protonated forms under certain conditions) can alter or lessen these effects. Understanding these directing effects is key to predicting the regiochemistry in reactions like aromatic bromination.

Electrophilic Aromatic Substitution (EAS)

Electrophilic aromatic substitution is a fundamental reaction mechanism in aromatic chemistry where an electron?rich aromatic ring reacts with an electrophile to replace one of its hydrogen atoms. The reaction proceeds via the formation of a sigma complex and is influenced by substituents present on the ring, which can either activate or deactivate the ring toward further substitution.

Acylation Reactions

Acylation involves the introduction of an acyl group (RCO–) into a molecule. When an amine reacts with an acyl chloride, the lone pair on nitrogen attacks the electrophilic carbonyl carbon, leading to the formation of an amide. This nucleophilic acyl substitution is often used to 'protect' an amine group, reducing its reactivity in subsequent reactions.

Hofmann Elimination

Hofmann elimination is a type of elimination reaction that occurs with quaternary ammonium salts. When a suitably substituted ammonium hydroxide is heated, a base-induced deprotonation at a beta-carbon relative to the nitrogen takes place, leading to the formation of an alkene and converting the quaternary ammonium into a tertiary amine. The reaction typically favors the less substituted (Hofmann) alkene.

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