Nitrogen atom that is a more basic among the two nitrogen atoms present in epibatidine has to be explained. Concept introduction: Amines are the derivatives of ammonia ( N H 3 ) with one or more of the hydrogens replaced with a substituent such as an alkyl group. Depending on the number of carbon side chain of the nitrogen, different types of amines can form. According to the explanations by Lewis, if a species donates an electron pair then it is a Lewis base whereas if a species receives an electron pair, then it is Lewis acid. Hybridization is the mixing of valence atomic orbitals to get equivalent hybridized orbitals that having similar characteristics and energy.

Question

Phenacetin is an analgesic compound having molecular formula C10H13NO2. Once a common component in over-the-counter pain relievers such as APC (aspirin, phenacetin, caffeine), phenacetin is no longer used because of its liver toxicity. Deduce the structure of phenacetin from its 1H NMR and IR spectra.

Answer 1

Question

Chapter 23, Problem 23.28P

(a)

Interpretation Introduction

Interpretation:

Nitrogen atom that is a more basic among the two nitrogen atoms present in epibatidine has to be explained.

Concept introduction:

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

According to the explanations by Lewis, if a species donates an electron pair then it is a Lewis base whereas if a species receives an electron pair, then it is Lewis acid.

Hybridization is the mixing of valence atomic orbitals to get equivalent hybridized orbitals that having similar characteristics and energy.

(b)

Interpretation Introduction

Interpretation:

Chiral centers in epibatidine have to be marked.

Concept Introduction:

Amines are the derivatives of ammonia (NH3) with one or more of the hydrogens replaced with a substituent such as an alkyl group.

Depending on the number of carbon side chain of the nitrogen, different types of amines can form.

Chirality: It refers to an atom in a molecule that contains four different substituents.

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