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Organic Chemistry 2 > Chapter 17- Aromatics > Flashcards

Chapter 17- Aromatics Flashcards

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1
Q

What is the product of Benzene and Br2?

A

No reaction!

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2
Q

How does aromaticity affect stabilization?

A

Enhanced stability

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3
Q

What is the criteria to be classified as an aromatic?

A
  1. cyclic
  2. continuous conjugation across atoms in cycle
  3. Planar
  4. Delocalized pi electrons (enhances stability)
  5. # of pi electrons equation
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4
Q

What is the equation (Huckel’s rule) for determining aromaticity?

A

pi electrons = 4N + 2

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5
Q

What is the criteria to be classified as an anti-aromatic?

A
  1. cyclic
  2. continuous conjugation across atoms in cycle
  3. Planar
  4. Delocalized pi electrons (Destabilized)
  5. # of pi electrons equation
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6
Q

What is the equation (Huckel’s rule) for determining antiaromaticity?

A

pi electrons = 4N

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7
Q

What is the criteria to be classified as Non Aromatic?

A
  • not cyclic
  • not planar
  • no continuous conjugation
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8
Q

Rank the stability of aromatic, antiaromatic and nonaromatic molecules

A

aromatic > nonaromatic > antiaromatic

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9
Q

What is the rule dealing with lone pairs of a heteroatom?

A

If the heteroatom’s lone pair is necessary for aromaticity, it will be counted in the Huckel number of pi electrons.

(only count 1 LP, not the other one, if there is one)

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10
Q

What is the general rule for Basicity?

A

If the lone pair is necessary for aromaticity, then the lone pair will not be basic

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11
Q

What is the general rule for Acidity?

A

If the loss of the proton provides an aromatic stabilized conjugate base, it is favorable.

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12
Q

What is important to remember when drawing MO diagrams

A
  • vertex down
  • cut shape in half
    -label bonding, n , and antibonding
    -lowest orbitals get filled first
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13
Q

Name this molecule.

A

chlorobenzene

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14
Q

Name this molecule.

A

nitrobenzene

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15
Q

Name this molecule.

A

Ethylbenzene

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16
Q

Name this molecule.

A

tetraphenylcyclopentadienone

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17
Q

Name this molecule.

A

Toluene

18
Q

Name this molecule.

A

phenol

19
Q

Name this molecule.

A

Anisole

20
Q

Name this molecule.

A

Aniline

21
Q

Name this molecule.

A

Benzoic acid

22
Q

Name this molecule.

A

benzaldehyde

23
Q

Name this molecule.

A

Acetophenone

24
Q

Name this molecule.

A

styrene

25
Q

What is this location name?

A

1,2 or ortho

26
Q

What is this location name?

A

1, 3 or meta

27
Q

What is this location name?

A

1,4 or para

28
Q

Name this molecule.

A

ortho-Nitroanisole
(2-Nitroanisole)

29
Q

Name this molecule.

A

meta-Bromotoluene
(3-Bromotoluene)

30
Q

Name this molecule.

A

para-Chlorobenzaldehyde

31
Q

Name this molecule.

A

1,3,5-trinitrobenzene

32
Q

Name this molecule.

A

2,4-dinitrophenol

33
Q

Name this molecule.

A

3,5-dihyroxybenzoic acid

34
Q

What word is used when benzene is not the priority functional group/root

A

phenyl

35
Q

What is the word for the group when the aromatic is substituted?

A

aryl group

36
Q

What word is used when there is an additional methylene linked to a phenyl

A

a benzyl group

37
Q

Where do ring vibrations show up on IR spectroscopy?

A

1450-1650cm-1

38
Q

Where do aromatic protons appear in 1H NMR?

A

6.5 to 8 ppm

39
Q

How does the integration of the 1H NMR help with determining structures?

A

Can determine symmetry and if there are multiple substituents off of the molecule

40
Q

Where do signals appear that typically indicate a benzene ring in a 13C NMR?

A

100 to 150ppm

41
Q

How can the number of signals from a 13C NMR help determine structure

A

The number of signals help determine the substitution pattern

Organic Chemistry 2 (14 decks)

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