Study Guide for Organic Chemistry: Structure and Reactivity, 5th Edition, by Ege by John Betancourt

Author:John Betancourt [Betancourt, John]
Language: eng
Format: azw3
Publisher: Clutch Prep
Published: 2016-08-10T16:00:00+00:00

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

PRACTICE: Draw the inscribed polygon for the following molecule.

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: BENZENE NOMENCLATURE

Benzene was one of the first organic molecules to be identified (1825), so common names predominate.

Common Benzene Derivatives:

___________ __________________ _________________

__________________ ___________________ _________________

_______________ _________________________ _________________

Monosubstituted Benzene: ● No location necessary Disubstituted Benzene: Multisubstituted Benzene: ● No numerical locations ● Numerical locations necessary □ 1,2 = __________ (o-) □ Do not use -o, -m, -p □ 1,3 = __________ (m-)

□ 1,4 = __________ (p-)

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

EXAMPLE: Correctly name the following benzene derivatives.

1.

2.

3.

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: ACIDITY OF AROMATIC HYDROCARBONS

Aromatic hydrocarbons are not naturally acidic. In fact, the pKa of benzene is ______

● If a hydrocarbon can become aromatic by donating a proton, it will be uniquely acidic. i.e. cyclopentadiene

● If a hydrocarbon becomes anitaromatic by donating a proton, it will be uniquely non-acidic. i.e. cycloheptatriene

EXAMPLE: Would the following hydrocarbon be expected to display unusual acidity? Explain your reasoning.

EXAMPLE: Would the following two hydrocarbons be expected to have similar acidities? Explain your reasoning.

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CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: ELECTROPHILIC AROMATIC SUBSTITUTION – GENERAL MECHANISM

Benzene reacts with very few reagents. It DOES NOT undergo typical addition reactions. Why?

If we can get benzene to react in a substitution reaction, this preserves aromaticity.

Very strong electrophiles can temporarily disrupt aromaticity of benzene to create a substitution product.

● We call this electrophilic aromatic substitution or __________. This is the most important mechanism of benzene.

EAS: General Mechanism

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CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: ELECTROPHILIC AROMATIC SUBSTITUTION – REACTIONS

EAS reactions require strong electrophiles to take place. Some of these will require catalysts.

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CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: GENERATING ELECTROPHILES – EAS HALOGENATION

EAS Bromination and Chlorination both require complexing with a Lewis Acid Catalyst before the reaction can begin.

General Reaction:

Mechanism:

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: GENERATING ELECTROPHILES – EAS NITRATION

EAS Nitration requires nitric acid to react with a catalytic acid to generate a strong nitronium ion electrophile.

General Reaction:

Mechanism:

Reduction of Nitro Groups:

Nitro groups can be reduced in the presence of many reducing agents to aniline. More on this in your amines chapter.

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: GENERATING ELECTROPHILES – FRIEDEL-CRAFTS ALKYATION

Friedel-Crafts Alkyation requires an alkyl halide to complex with a Lewis Acid Catalyst before the reaction can begin.

● Active electrophile is a carbocation

□ Watch out for ________________________________

General Reaction:

Mechanism:

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: GENERATING ELECTROPHILES – FRIEDEL-CRAFTS ACYLATION

Friedel-Crafts Acylation requires an acyl halide to complex with a Lewis Acid Catalyst before the reaction can begin.

● Active electrophile is an acylium ion

General Reaction:

Mechanism:

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: GENERATING ELECTROPHILES – ANY CARBOCATION

Popular carbocations include those catalyzed by hydrofluoric acid and promoted by boron trifluoride.

● Watch out for ________________________________

General Reaction:

Mechanisms:

CH. 10 - THE CHEMISTRY OF AROMATIC COMPOUNDS

CONCEPT: EAS –

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