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Predict the major products formed when the following

Chapter 13, Problem 20P

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QUESTION:

Predict the major products formed when the following amines undergo exhaustive methylation,

treatment with \(\mathrm{Ag}_{2} \mathrm{O}\), and heating.

(a) hexan-2-amine

(b) 2-methylpiperidine

(c) N-ethylpiperidine

Equation transcription:

Text transcription:

{Ag}{2} {O}

Questions & Answers

QUESTION:

Predict the major products formed when the following amines undergo exhaustive methylation,

treatment with \(\mathrm{Ag}_{2} \mathrm{O}\), and heating.

(a) hexan-2-amine

(b) 2-methylpiperidine

(c) N-ethylpiperidine

Equation transcription:

Text transcription:

{Ag}{2} {O}

ANSWER:

Solution 20P

(a)

Treatment of 2-hexanamine with excess methyl iodide forms a quaternary ammonium salt. Now, the silver oxide, replaces the iodide anion with a strong base. Next the ammonium salt is heated (-OH removes a proton from the  carbon atom) and forms a new  bond of the alkene. Thus, the possibility of the formation the alkenes is shown in the reaction and major alkene is represented with the less substituted double bond.

(b)

Treatment of 2-methylpiperidine with excess methyl iodide forms a quaternary ammonium salt. Now, the silver oxide, replaces the iodide anion with a strong base. Next the ammonium salt is heated (-OH removes a proton from the  carbon atom) and forms a new  bond of the alkene. Thus, the possibility of the formation the alkenes is shown in the reaction and major alkene is represented with the less substituted double bond.

(c)

Treatment of

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