Resonance structures of 3-methyl anisole have to be drawn. Concept Introduction: Resonance is an electron displacement effect for stabilizing a molecule through delocalization of bonding electrons in the pi orbital. Delocalized electrons stabilize a compound. The extra stability gains from having delocalized electrons are called resonance stabilization or resonance energy.

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Chapter 17.7, Problem 21ATS

(a)

Interpretation Introduction

Interpretation:

Resonance structures of 3-methyl anisole have to be drawn.

Concept Introduction:

Resonance is an electron displacement effect for stabilizing a molecule through delocalization of bonding electrons in the pi orbital.

Delocalized electrons stabilize a compound. The extra stability gains from having delocalized electrons are called resonance stabilization or resonance energy.

(b)

Interpretation Introduction

Interpretation:

More dominant factor among the resonance effect and the inductive effect for the methoxy substituent has to be identified based on the given Birch reaction.

Concept Introduction:

Resonance is an electron displacement effect for stabilizing a molecule through delocalization of bonding electrons in the pi orbital.

Delocalized electrons stabilize a compound. The extra stability gains from having delocalized electrons are called resonance stabilization or resonance energy.

Inductive effect: It is an electronic effect occurs due to the difference in the electronegativity of atoms in a bond. This unequal sharing of electrons in the bond leads to a permanent dipole.

In Birch reduction, the benzene ring undergoes 1,4 reduction where unconjugated cyclohexadienes are formed.

If the benzene ring has an electron donating substituent, the double bond next to it does not get reduced in Birch reduction.

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C 5 4 3 CI 2 the Righ B A 5 4 3 The Lich. OH 10 4 5 3 1 LOOP- -147.52 T 77.17 -45.36 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm B -126.25 77.03 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 200 190 180 170 160 150 140 130 120 110 100 90 80 TO LL <-50.00 70 60 50 40 30 20 10 ppm 45.06 30.18 -26.45 22.36 --0.00 45.07 7.5 1.93 2.05 -30.24 -22.36 C A 7 8 5 ° 4 3 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 8 5 4 3 ཡི་ OH 10 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 5 4 3 2 that th 7 I 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 115 2.21 4.00 1.0 ppm 6.96 2.76 5.01 1.0 ppm 6.30 1.00