Acetanilide is less reactive than aniline toward electrophilic substitution. Explain. (EQUATION

step 1 Okay, so a very similar question to 16 .11. We're comparing anilin to acetanilide now. So do you

Acetanilide is less reactive than aniline toward...

Key Concepts

Substituent Effects on Aromatic Reactivity

Substituents attached to the aromatic ring can either activate or deactivate the ring toward electrophilic attack. Electron-donating groups increase the electron density on the ring through resonance or inductive effects, making it more reactive toward electrophiles. Conversely, electron-withdrawing groups decrease the electron density, rendering the ring less reactive. The overall reactivity in electrophilic aromatic substitution reactions is determined by the nature and position of these substituents.

Electrophilic Aromatic Substitution

This is a reaction mechanism in which an electrophile replaces a hydrogen atom on an aromatic ring. The process involves the initial formation of a sigma complex (or arenium ion), followed by a deprotonation step to restore aromaticity. The rate and outcome of the reaction are highly dependent on the electron density of the aromatic ring, which is affected by the substituents present on the ring.

Resonance and Inductive Effects

Resonance effects involve the delocalization of electrons through conjugated systems, which can either stabilize or destabilize intermediates during the reaction. Inductive effects relate to the transfer of electron density through sigma bonds due to differences in electronegativity. When a functional group that is normally electron-donating is modified by an electron-withdrawing group, its ability to donate electrons through resonance is hindered, resulting in a decrease in the overall reactivity of the aromatic ring.

Transcript

00:01 Okay, so a very similar question to 16 .11.

00:04 We're comparing anilin to acetanilide now.

00:08 So do you think anilin is more or less reactive than a set of nilite to a logophilic substitution? so this is relevant for your resident structures, right? so you may be familiar, and i definitely recommend practicing your arrow pushing.

00:25 Right.

00:26 So let's say you have anilin here.

00:28 Here, you're able to arrive at a carbocadion structure where you have your new electrophile added here and your most stable resident structure being where you have the electron donating group on the same carbon as your carbocation.

00:49 So you're able to donate electron density directly into that atom and arrive at a more see if i can draw this right, a more stable residence form where your positive charge is now on your nitrogen.

01:09 Right? so that being the most contributing factor to why ortho ortho or para position for electron donating groups orthor or power adding is more favored or why these donating groups favor ortho power addition is because it allows you to arrive at these resident structures that are highly stabilized, right? so, which you don't see with meta, for example.

01:39 You can't get to that structure through conventional error portion using with a meta added electrophile intermediate.

01:46 So take a set an eyelid now.

01:48 So right, so you can still arrive at these same intermediates here.

01:56 You can still do what i just did...

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