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Organic Chemistry > Aromatics > Flashcards

Aromatics Flashcards

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1
Q

Aromaticity

A

What makes a system aromatic or not aromatic.

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2
Q

4 conditions of Aromaticity

A
  1. Cyclic
  2. Each carbon is sp2
  3. Continuous loop of p-orbitals
  4. Hachel’s Rule satisfied
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3
Q

Hachel’s Rule

A

of e- in p-loop = 4n+2 or # of π e- = 4n + 2

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4
Q

Parent name for simple compounds

A

Benzene

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5
Q

Nitro

A

NO2

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6
Q

NH2 attached to benzene

A

Aniline

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7
Q

isopropyl attached to benzene

A

Cumene

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8
Q

ethene attached to benzene

A

Styrene

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9
Q

OH attached to benzene

A

Phenol

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10
Q

Carbonyl attached to benzene

A

Benzaldehyde

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11
Q

Carboxylic acid attached to benzene

A

Benzoic Acid

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12
Q

Ether attached to Benzene

A

Anisole

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13
Q

Ketone attached to Benzene

A

Acetophenone

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14
Q

Dimethylbenzene

A

Zylene

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15
Q

Electrophilic Aromatic Substitution, why does it include the word “substitution”?

A

Hydrogen is being substituted for electrophile.

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16
Q

Electrophilic Aromatic Substitution Requirements

A

Strong Electrophile, Look at resonance (at least 3)

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17
Q

Is the carbocation intermediate of the electrophilic aromatic substitution stable? Why?

A

It is stable, because it is resonance stabilized.

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18
Q

Steps of Electrophilic Aromatic Substitution

A
  1. Formation of Electrophile
  2. Formation of Arenium Ion
  3. Regeneration of Aromatic Ring
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19
Q

halogens don’t like what?

A

positive charge

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20
Q

Chlorination and Bromination Requirement

A

Requires Lewis Acid Catalyst

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21
Q

Lewis Acid Catalysts

A

For Cl2: FeCl3 or AlCl3

For Br2: FeBr3 or AlBr3

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22
Q

Nitric Acid

A

HNO3

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23
Q

Which one is a stronger acid? Sulfuric Acid or Nitric Acid?

A

Sulfuric Acid (H2SO4) is a stronger acid than HNO3

24
Q

Bronsted Lowry Acid

A

Proton donor (not an acceptor like Lewis Acid)

25
Q

Bronsted Lowry Base

A

Proton Acceptor

26
Q

Required reagents for nitration

A

Nitric Acid, Sulfuric Acid, and heat

27
Q

Difference between nitration, sulfonation, and halogenation

A

Only difference is how you form electrophile.

28
Q

Required reagents for sulfonation

A

SO3 and H2SO4

29
Q

SO3

A

Sulfur Trioxide.

30
Q

Sulfonation resulting product

A

Benzene sulfonic Acid - SO3H added to Benzene

31
Q

Thing to remember about carbocations

A

LOOK FOR REARRANGEMENT

32
Q

How many products are generated from friedel-crafts alkylation?

A

2 without resonance, 1 without rearrangement (minor)

33
Q

Friedel-Crafts Alkylation Limitations

A

Rearrangement possibility and Electron withdrawing groups

34
Q

Why are electron withdrawing groups a limitation for Friedel-Crafts Alkylation?

A

Electron Withdrawing groups reduce the electron density of the ring and make it less likely that electrons will go to chloride, resulting in no reaction.

35
Q

Required Reagent for Friedel-Crafts Acylation

A

Acyl Chloride and AlCl3 like alkylation

36
Q

Limitation of Friedel-Crafts Acylation

A

Rearrangement still can occur.

37
Q

Electrophile used for Friedel-Crafts Acylation

A

Acylium ion

38
Q

What limitation does Friedel-Crafts Acylation resolve?

A

Electron withdrawing group results in no reaction - problem of Alkylation

39
Q

What does Clemmensen Reduction do?

A

Remove ketone after acylation.

40
Q

What we don’t need to know about Clemmensen Reduction

A

its mechanism, just now its reagents.

41
Q

Where is the benzylic carbon?

A

First Carbon attached to Benzene

42
Q

Oxidation at Benzylic Carbon results in what?

A

Formation of Carboxylic group

43
Q

Oxidation at Benzylic Carbon requires what reagents?

A

KMnO4, heat, H3O+, and NaOH

44
Q

What leads to no reaction for oxidation at Benzylic Carbon?

A

Benzylic carbon has no hydrogens and no π bonds.

45
Q

Downside of oxidation at benzylic carbon

A

Difficult to control, affects multiple functional groups

46
Q

Oxidation at benzylic carbon further group terms for pi bonds

A

Alkenyl group, Alkynyl Group

47
Q

Ortho and Para products. Which on is major? Why?

A

Para, because of steric effect. (less steric hindrance)

48
Q

First substituent has what effect on the second substituent?

A

The first substituent has two effects on the second substituent: the first substituent can either be ortho/para directing or meta directing, and the first substituent can alter the rate of the second substituent. Activating = speeds up reaction, deactivating = slows down reaction.

49
Q

What mechanical way determines whether a substituent is ortho/para directing or meta directing?

A

Number of resonance structures and full octet.

50
Q

Ortho/para directors characteristics

A

Ortho/para directors have a lone pair of electrons and are electron donating.

51
Q

Meta director characteristics

A

Electron withdrawing (except halogens).

52
Q

Common ortho/para directors

A

-OR, -NR2, -R, -X (inappropriate films) - R=alkyl, acyl (carbonyl), H

53
Q

Activating Substituents characteristics

A

Usually ortho/para directors excluding halogens.

54
Q

Deactivating Substituents Characteristics

A

Electron withdrawing groups

55
Q

Why are most electron withdrawing groups deactivators?

A

Because they reduce electron density of the ring, slowing down the reaction.

56
Q

In order to add a third substituent, which substituent is the driving force behind determining where it will go?

A

Activating substituent is stronger than the deactivating substituent, so it will determine where the third substituent goes.

57
Q

TNT

A

2,4,6 - Trinitrotoluene

Organic Chemistry (4 decks)

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