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26. Amines

Cope Elimination

26. Amines

Cope Elimination

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General Reaction

General Reaction

Johnny Betancourt

Johnny Betancourt

Predict the Product

Predict the Product

Johnny Betancourt

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Multiple Choice

Which of the following successfully synthesizes the given target?

Textbook Question

Using any necessary reagents, show how you would accomplish the following syntheses. (e) <

of reaction> (f) <

Textbook Question

Predict the products of the following reactions: (c) <

of reaction> (d) <

Textbook Question

What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat? d.

Textbook Question

What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat? c.

Textbook Question

A tertiary amine reacts with hydrogen peroxide to form a tertiary amine oxide. Tertiary amine oxides undergo a reaction similar to the Hofmann elimination reaction (Section 10.10), called a Cope elimination. In this reaction, a ter- tiary amine oxide, rather than a quaternary ammonium ion, undergoes elimination. A strong base is not needed for a Cope elimination because the amine oxide acts as its own base. Does the Cope elimination have an alkene-like transition state or a carbanion-like transition state?

Textbook Question

Give the products expected when the following tertiary amines

are treated with a peroxyacid and heated.

(a) N,N-dimethylhexan-2-amine

Textbook Question

Give the products expected when the following tertiary amines

are treated with a peroxyacid and heated.

(b) N,N-diethylhexan-2-amine

Textbook Question

Give the products expected when the following tertiary amines

are treated with a peroxyacid and heated.

(c) cyclohexyldimethylamine

Textbook Question

Give the products expected when the following tertiary amines

are treated with a peroxyacid and heated.

(d) N-ethylpiperidine

Predict the products of the following reactions:

(i) <IMAGE of reaction>

Textbook Question

What products are obtained when the following tertiary amines react with hydrogen peroxide followed by heat?

a. <IMAGE>

b. <IMAGE>

Textbook Question

Predict the products of the following reactions:

(g) <IMAGE of reaction>

Textbook Question

Predict the products of the following reactions:

(i) <IMAGE of reaction>

Textbook Question

When the (R,R) isomer of the amine shown is treated with

an excess of methyl iodide, then silver oxide, then heated,

the major product is the Hofmann product.

(b) Some Zaitsev product is also formed. It has

the (E) configuration. When the same amine is treated

with mCPBA and heated, the Zaitsev product has

the (Z) configuration. Use stereochemical drawings

of the transition states to explain these observations.

<IMAGE of reactions>

Textbook Question

In Section 21-16, we saw that Sevin insecticide is made by the reaction of 1-naphthol with methyl isocyanate. A Union Carbide plant in Bhopal, India, once used this process to make Sevin for use as an agricultural insecticide. On December 3,1984, either by accident or by sabotage, a valve was opened that admitted water to a large tank of methyl isocyanate. The pressure and temperature within the tank rose dramatically, and pressure-relief valves opened to keep the tank from bursting.

A large quantity of methyl isocyanate rushed out through the pressure-relief valves, and the vapors flowed with the breeze into populated areas, killing about 2500 people and injuring many more.

(a) Write an equation for the reaction that took place in the tank. Explain why the pressure and temperature rose

dramatically.

(b) Propose a mechanism for the reaction you wrote in part (a).

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