Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 13, Problem 54P
Interpretation Introduction

Interpretation:

The resonating structures and resonance hybrid for the carbocation that could result from the ionization of bromine from 5bromo1,3pentadiene are to be drawn. Based on the model, the most important contributing resonance structure for this cation is to be predicted.

Concept introduction:

Resonance means delocalization of electrons within a molecule. It is also known as mesomerism.

A molecule in which delocalization of electron takes place is shown by various contributing structures and these contributing structures are called resonating structures.

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1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts. Which of the following correctly describes this new resonance structure? a) It has a double bond between carbons 3 and 4 b) It has a positive charge on carbon 2 c) It has a positive charge on carbon 4 d) It has a double bond between carbons 2 and 3
4. A certain endothermic reaction X carried out room temperature (273K) has an enthalpy change of 20 Kcal/mol and an entropy change of 10 Kcal/K/mol. i) Calculate the Gibbs free energy (AG) of this reaction. ii) Is this reaction spontaneous or non-spontaneous? Give a reason for your answer 5. Thiomethane reacts with compound A via an SN1 reaction. Complete its reaction equation below. ii) SH Compound A ii) Draw the mechanism of reaction for this reaction. 6. Butyl Chloride undergoes an elimination reaction when reacted with sodium ethoxide to form butene. The reaction equation is given below with two reaction products A and B. low inevloa CI noitsups p *OEt B Which is the major product, and which is minor product. (Hint: Look up how the size of the base affects the elimination reaction product) Give a reason for your answer.
Read these directions carefully. For the reaction of 3-methyl-1-propene with Cl2 and H2O shown below, fill in the details of the mechanism. Draw the appropriate chemical structures and use an arrow to show how pairs of electrons are moved to make and break bonds during the reaction. Be sure to write all lone pairs of electrons and all formal charges. Finally, in the boxes provided by the arrows, write which kind of mechanistic element is being indicated, such as "make a bond", "add a proton", etc.

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Organic Chemistry

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