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 6, Problem 8PP
Interpretation Introduction

Interpretation:

The structure of carbocation and the products formed on the reaction of iodocyclohexane with water are to be written.

Concept Introduction:

Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.

Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Nucleophilic substitution reaction is a reaction in which an electron rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.

SN2 reaction is the nucleophilic substitution reaction in which the two components are involved in the rate determining step.

The SN2 mechanism of substitution reaction occurs in secondary alkyl halides with an inversion of configuration.

The SN2 reaction takes place in one step. The nucleophile attacks the alkyl halide from the side opposite to the leaving group, resulting in an inversion of configuration.

An SN1 reaction is a nucleophilic substitution reaction in which only one component is involved in the rate-determining step.

The nucleophilic substitutions in which a nucleophile replaces a leaving group are known as SN1 reactions.

SN1 reactions are unimolecular as the rate of reaction is dependent on the concentration of a single reactant.

Carbocation is a molecule having a carbon atom bearing three bonds and a positive formal charge.

Carbocation are generally unstable because they do not have eight electrons to satisfy the octet rule.

The order of stability of carbocation is such that the tertiary carbocation is the most stable whereas the primary carbocation is the least stable, and secondary carbocation lies between primary and tertiary carbocations.

If primary carbocation is obtained in product, it rearranges itself to secondary or tertiary carbocation to form more stable product.

If secondary carbocation is obtained in product, it rearranges itself to tertiary carbocation to form more stable product.

The stability of carbocation:

3ocarbocation>2ocarbocation>1ocarbocation>methylcarbocation

The SN1 reaction of nucleophilic substitution reactions takes place in two steps.

In the first step, the alkyl halide ionizes to form a carbocation and halide ion.

In the second step, the nucleophile attacks the carbocation to form the product.

The carbocation is trigonal planar in structure and hence, the nucleophile can attack from both the sides to form two products.

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PRACTICE PROBLEM 6.5 Using chair conformational structures (SectionA), show the nueleophilie substitution reaction that would take place when trans-1-bromo-4-tert-butyleyclohexane reacts with lodide lon. (Show the most stable conformnation of the reactant and the product.) Sy2 reactions always occur with inversion of configuration
• PRACTICE PROBLEM 8.24 A, B, and C are alkynes. Elucidate their structures and that of D using the following reaction roadmap. H2, Pt H,, Pt A (C3H14) (C3H14) IR: 3300 cm (1) O3 (2) HOẠC HO, H2, Pt (C3H12) (C3H16) (1) O3 (2) HOAC hol bian vd beeollot Но. ОН AOH
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