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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

Propose a mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride

a. What is the product of the reaction of acetyl chloride withHO-? ThepKaof HCl is -7; thepKaofH2Ois 15.7.

b. What is the product of the reaction of acetamide withHO-? ThepKaofNH3is 36; thepKaofH2Ois 15.7.

An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product isformed? Explain.

Two products, A and B, are obtained from the reaction of 1-bromobutane with NH3 . Compound A reacts with acetyl chloride to form C, and compound B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.

Identify the major and minor products of the following reaction:
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