Thermal electrocyclic ring closure of (2Z, 4Z, 6Z)-2,4,6-octatriene yielding products via conrotatory and disrotatory cyclizations. Concept introduction: Conrotatory and disrotatory is based on the rotation at each end of the molecule. In conrotatory mode, both atomic orbitals of the end groups turn in the same direction ,such as both atomic orbitals rotating clockwise or counter-clockwise. In disrotatory mode, the atomic orbitals of the end groups turn in opposite directions ,one atomic orbital turns clockwise and the other counter-clockwise. The cis/trans geometry of the final product is directly decided by the difference between conrotation and disrotation. Whether a particular reaction is conrotatory or disrotatory can be accomplished by examining the molecular orbitals of each molecule and through a set of rules. Only two pieces of information are required to determine conrotation or disrotation using the set of rules: how many electrons are in the pi-system and whether the reaction is induced by heat or by light. This set of rules can also be derived from an analysis of the molecular orbitals for predicting the stereochemistry of electrocyclic reactions.

Question

B 1 of 2 Additional problems in preparation to Midterm #1: 1.) How can the following compounds be prepared using Diels-Alder reaction: CH3 O CN (a) (b) CN CH3 2.) What is the missing reagent in the shown reaction? H3C + ? H3C H3C CN H3C ''CN (၁) H 3.) Write the products 1,2-addition and 1,4-addition of DBr to 1,3-cyclohexadiene. Remember, D is deuterium, a heavy isotope of hydrogen. It reacts exactly like hydrogen. 4.) In the shown reaction, which will be the kinetic product and which will be the thermodynamic product? H3C CI H3C HCI H3C + 5.) Which of the following molecules is aromatic? (a) (b) (c) H 6.) Which of the following molecules is aromatic? (a) (b) (c) 7.) Write the mechanism for the shown reaction. + Ха AICI 3 CI 8.) Suggest reagents that would convert benzene into the shown compounds. CI NO2 -8-6-6-8-a (a) (b) (c) (d) (e) (a) SO3H Br

Answer 1

Question

Chapter 30.3, Problem 2P

Interpretation Introduction

Interpretation:

Thermal electrocyclic ring closure of (2Z, 4Z, 6Z)-2,4,6-octatriene yielding products via conrotatory and disrotatory cyclizations.

Concept introduction:

Conrotatory and disrotatory is based on the rotation at each end of the molecule. In conrotatory mode, both atomic orbitals of the end groups turn in the same direction ,such as both atomic orbitals rotating clockwise or counter-clockwise. In disrotatory mode, the atomic orbitals of the end groups turn in opposite directions ,one atomic orbital turns clockwise and the other counter-clockwise. The cis/trans geometry of the final product is directly decided by the difference between conrotation and disrotation.

Whether a particular reaction is conrotatory or disrotatory can be accomplished by examining the molecular orbitals of each molecule and through a set of rules. Only two pieces of information are required to determine conrotation or disrotation using the set of rules: how many electrons are in the pi-system and whether the reaction is induced by heat or by light. This set of rules can also be derived from an analysis of the molecular orbitals for predicting the stereochemistry of electrocyclic reactions.

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