Write the overall reaction for reaction of methyl benzoate with excess phenyl magnesium brimide in ether, followed by H3O+. ????
The mechanism for this is something like this:
- The magnesium bromide acts as a Lewis acid, turning the phenyl group into a nucleophile. Naturally, it backside-attacks the most susceptible electrophilic center, forming a fairly sterically-hindered tetrahedral intermediate. It is excess reactant so that it happens to a reasonable yield.
- The negatively-charged oxygen grabs a proton from the acid that you add afterwards.
- Electron conjugation from the newly-formed hydroxyl group's oxygen forces the methoxy leaving group to break off, a rapid intramolecular process. The pKa of methanol is about
#15.5# , but the pKa of benzene is about#43# , so there is pretty much no chance (#1# in#10^27.5)# of the phenyl group breaking back off.- The reaction finishes when the methanolate grabs the proton off of the protonated final product. The methanolate does so rather than the water (
#10^6.1# times as often), since the pKa of methanol (#~15.5# ) is greater than the pKa of hydronium (#~9.4# ), and acid-base equilibrium lies on the side of the weaker acid or stronger base.- Repeat the curved arrows and electron flow in steps 1 and 2 with another equivalent of phenyl magnesium bromide.
Your final product is triphenylmethanol.
By signing up, you agree to our Terms of Service and Privacy Policy
The overall reaction for the reaction of methyl benzoate with excess phenyl magnesium bromide in ether, followed by H3O+ is:
Methyl benzoate + Phenyl magnesium bromide → Benzophenone + Magnesium bromide + Methanol
The benzophenone is then protonated by H3O+ to yield the final product.
By signing up, you agree to our Terms of Service and Privacy Policy
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.
When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

- 98% accuracy study help
- Covers math, physics, chemistry, biology, and more
- Step-by-step, in-depth guides
- Readily available 24/7