Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 13, Problem 2PP
Interpretation Introduction

Interpretation:

The resonance structures for the carbocation formed by (E)2butenyltrifluoromethanesulfonate are to be drawn and the resonance structure that contribute greater to the hybrid is to be determined. Also the products formed by the reaction of carbocation with a chloride ion are to be determined.

Concept introduction:

Secondary and tertiary carbocations are more stable than a primary carbocation.

Resonance is defined as the movement of pi-electrons from one carbon to another in order to stabilize the charged intermediates.

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The following compound, 2-hydroxycycloheptatrienone, does not give all the usual carbonyl group reactions. (i) Explain this apparent anomaly. Furthermore, explain the significant difference between the relative stability of this compound and its 3- and 4-hydroxy isomers. (ii) What would you expect to be the influence of adding (a) a nitro group as a substituent on the 7-membered ring or (b) an alkyl group, on the degree of aromaticity of the above compound. (iii) Based on your understanding of the hydrogen bonding concept, which isomer would you expect to have a higher m.p, (assuming they are both solids) between 2- and 4- hydroxycycloheptatrienone? Explain your choice.
Provide concise syntheses for each of the following compounds starting from but-1 - ene. The source of all the carbon atoms in these molecules must be either but-1 - ene or any one carbon nucleophile/electrophile. (If you must use a reagent that has more than one carbon atoms you must show the preparation of that reagent from but-1 - ene.) (a) Methyl propanoate (b) 3, 5- Dimethylheptan-4-one (c) 5-ethyl-7-methylnon-4-ene
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Organic Chemistry

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