Plausible mechanism for the given set of transformation needs to be proposed. Concept introduction: When a diketone is deprotonated to form a doubly stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α,β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. If the addition reaction takes place within the same molecule means then it is known as intramolecular Michael addition reaction. A general scheme for Michael addition is shown below, To Propose : To propose a plausible mechanism for the given transformation.

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Chapter 21, Problem 100IP

(a)

Interpretation Introduction

Interpretation:

Plausible mechanism for the given set of transformation needs to be proposed.

Concept introduction:

When a diketone is deprotonated to form a doubly stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α,β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. If the addition reaction takes place within the same molecule means then it is known as intramolecular Michael addition reaction. A general scheme for Michael addition is shown below,

To Propose : To propose a plausible mechanism for the given transformation.

(b)

Interpretation Introduction

Interpretation:

Plausible mechanism for the given set of transformation needs to be proposed.

Concept introduction:

When a diketone is deprotonated to form a doubly stabilized enolate ion (Michael donor) which acts as a nucleophile for 1,4-conjugate addition to α,β -unsaturated compound (Michael acceptor) is known as Michael reaction. Michael reaction is thermodynamically controlled. If the addition reaction takes place within the same molecule means then it is known as intramolecular Michael addition reaction. A general scheme for Michael addition is shown below,

To Propose : To propose a plausible mechanism for the given transformation.

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Part I. a) Elucidate the structure of compound A using the following information. • mass spectrum: m+ = 102, m/2=57 312=29 • IR spectrum: 1002.5 % TRANSMITTANCE Ngg 50 40 30 20 90 80 70 60 MICRONS 5 8 9 10 12 13 14 15 16 19 1740 cm M 10 0 4000 3600 3200 2800 2400 2000 1800 1600 13 • CNMR 'H -NMR Peak 8 ppm (H) Integration multiplicity a 1.5 (3H) triplet b 1.3 1.5 (3H) triplet C 2.3 1 (2H) quartet d 4.1 1 (2H) quartet & ppm (c) 10 15 28 60 177 (C=0) b) Elucidate the structure of compound B using the following information 13C/DEPT NMR 150.9 MHz IIL 1400 WAVENUMBERS (CM-1) DEPT-90 DEPT-135 85 80 75 70 65 60 55 50 45 40 35 30 25 20 ppm 1200 1000 800 600 400

• Part II. a) Elucidate The structure of compound c w/ molecular formula C10 11202 and the following data below: • IR spectra % TRANSMITTANCE 1002.5 90 80 70 60 50 40 30 20 10 0 4000 3600 3200 2800 2400 2000 1800 1600 • Information from 'HAMR MICRONS 8 9 10 11 14 15 16 19 25 1400 WAVENUMBERS (CM-1) 1200 1000 800 600 400 peak 8 ppm Integration multiplicity a 2.1 1.5 (3H) Singlet b 3.6 1 (2H) singlet с 3.8 1.5 (3H) Singlet d 6.8 1(2H) doublet 7.1 1(2H) doublet Information from 13C-nmR Normal carbon 29ppm Dept 135 Dept -90 + NO peak NO peak 50 ppm 55 ppm + NO peak 114 ppm t 126 ppm No peak NO peak 130 ppm t + 159 ppm No peak NO peak 207 ppm по реак NO peak

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