Chapter 17

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Aromaticity

24 Terms

1

What is the first of Hunckel’s rules of Aromaticity vs Antiaromatic?

Is the compound cyclic

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2

What is the second of Hunckel’s rules of Aromaticity vs Antiaromatic?

Is the compound planar

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3

What is the third of Hunckel’s rules of Aromaticity vs Antiaromatic?

Completely conjugated (all overlapping p-orbitals)

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4

What is the fourth of Hunckel’s rules of Aromaticity vs Antiaromatic?

(4n+2) π electrons if aromatic; 4n π electrons if anti aromatic (where n is a whole number)

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5

What is the shortcut for aromaticity in a cyclic compound without lone pairs?

If the number of π bonds is odd then the compound is aromatic, but if the number of π bonds is even then the compound is anti-aromatic.

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6

What is the biggest thing that must be paid attention to when determining aromaticity?

Lone Pairs

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7

Why does an aromatic compound not undergo electrophilic addition, but instead only undergoes substitution i the presence of a Lewis Acid?

This is because the aromatic system is stabilized by resonance, and electrophilic addition would disrupt this stability, whereas substitution preserves the aromatic character.

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8

Orbitals above the non-bonding line in MO theory are called what?

The antiboding orbitals. which lead to instability if filled.

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9

What do you call orbiatals below the non-bonding line in MO theory?

The bonding orbitals, which lead to stability.

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10

What are the name of two or more orbitals at the same energy level?

Degenerate orbitals.

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11

What us the Frost Circle diagram?

A graphical representation used to visualize the molecular orbitals of cyclic compounds, showing how atomic orbitals combine to form molecular orbitals.

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12

How do you orient a compound inside of a frost circle?

The vertex is pointed down, and where the corners of the cyclic ring touch the circle are the orbitals.

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13
<p>For cyclic compounds with adjacent π bonds that are trans, similar to this picture. What happens?</p>

For cyclic compounds with adjacent π bonds that are trans, similar to this picture. What happens?

The compound is strerically hindered and cannot be planar.

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14
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

Phenol (PhOH)

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15
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

Anisole

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16
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

Aniline

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17
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

benzoic acid

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18
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

benzaldehyde

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19
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

acetophenone

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20
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

toulene

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21
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

xylines (ortho-, meta-, para-)

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22
<p>What is the common name of the following molecule?</p>

What is the common name of the following molecule?

Styrene

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23
<p>As a substituent what is the following molecule known as?</p>

As a substituent what is the following molecule known as?

Phenyl (ph) [C6H5-R]

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24
<p>As a substituent what is the following molecule known as?</p>

As a substituent what is the following molecule known as?

benzyl (Br)

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