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Chapter 15: Q90P (page 738)

Propose a mechanism that accounts for the formation of the product.

Short Answer

Expert verified

The proposed mechanism is shown below.

Step by step solution

01

Attack of proton

The proton attacks the hydroxide ion and forms water. When this water molecule is removed, electron delocalization occurs.

Attack of proton

02

Cyclization of molecule

The lone pair of electron in nitrogen atom is shifted to pentene and the double bond in the pentene is shifted and becomes a single bond.


Cyclization of molecule

03

Release of Bronsted Acid BH+

BH+ is released after cyclisation and electron delocalization. So nitrogen forms a positive charge on it and the final product is obtained.

Release of Bronsted Acid BH+

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Most popular questions from this chapter

When butanoic acid and 18O-labelled methanol react under acidic conditions, what compounds are labelled when the reaction has reached equilibrium?

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

Which alkyl halides form the carboxylic acids listed hereafter reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?

a. butyric acid

b. isovaleric acid

c. cyclohexane carboxylic acid

When treated with an equivalent of methanol, compound A, with the molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.

Question: Draw a structure for each of the following:

a. N,N-dimethylhexanamide

b. 3,3-dimethylhexanamide

c. Cyclohexanecarbonyl chloride

d. Propanenitrile

e. propionamide

f. sodium acetate

g. benzoic anhydride

h. b-valerolactone

i. 3-methylbutanenitrile

j. cycloheptanecarboxylic acid

k. benzoyl chloride

See all solutions

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