Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bond-making steps. 0: Select to Add Arrows 10: HO CI: O Select to Add Arrows :0: Select to Add Arrows

Question

Anu Bhardwaj · Accepted Answer

Step 1: Nucleophilic attack

The amine lone pair (–NH₂) attacks the electrophilic carbon attached to the leaving group (Cl) in the nitrobenzyl chloride.
Draw an arrow from the lone pair on nitrogen to the benzylic carbon.
Simultaneously, draw an arrow from the C–Cl bond to chlorine (Cl leaves as Cl⁻).

Step 2: Formation of tetrahedral intermediate

After the nucleophilic attack, nitrogen is positively charged (since it has 4 bonds).
Chloride (Cl⁻) is now a free anion in solution.
The nitro group (–NO₂) stabilizes the benzylic position through resonance.

Step 3: Proton transfer

A proton transfer step occurs: one of the N–H hydrogens is deprotonated (either by Cl⁻ or by base present).
Draw an arrow from the Cl⁻ (or base) to the hydrogen on nitrogen, and from the N–H bond to nitrogen.

Step 4: Final product

You end up with a neutral secondary amine attached to the benzyl group (–CH₂–NH–).
The leaving group is HCl.

✅ Summary of Curved Arrows You Need to Draw:

Lone pair on N → benzylic carbon.
C–Cl bond → Cl atom.
Cl⁻ lone pair → H of N–H.
N–H bond → N.

Chemistry

Chemistry

Anu Bhardwaj

Answer

Extracted Transcript from Images