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Organic Chemistry > Aromatic Compounds > Flashcards

Aromatic Compounds Flashcards

1
Q

Monosubstituted derivatives of benzene are named systematically using __________ as the parent & the substituent as a prefix

A

Benzene (Ex. Chlorobenzene)

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2
Q

What is the common name of this compound? (monosubstituted compound)

A

Toluene

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3
Q

What is the common name of this compound? (monosubstituted compound)

A

Phenol

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4
Q

What is the common name of this compound? (monosubstituted compound)

A

Anisole

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5
Q

What is the common name of this compound? (monosubstituted compound)

A

Aniline

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6
Q

What is the common name of this compound? (monosubstituted compound)

A

Benzoic Acid

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7
Q

What is the common name of this compound? (monosubstituted compound)

A

Benzaldehyde

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8
Q

What is the common name of this compound? (monosubstituted compound)

A

Acetophenone

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9
Q

What is the common name of this compound? (monosubstituted compound)

A

Styrene

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10
Q

If a substituent is larger than the benzene ring, then the benzene ring is treated as a substituent & called __________

A

Phenyl Group (Ex. 1-phenylheptane)

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11
Q

Dimethyl derivatives of benzene are called ___________

A

Xylene

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12
Q

What are the 3 constitutionally isomeric xylenes?

A
  1. ortho-Xylene
  2. Meta-Xylene
  3. Para- Xylene
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13
Q

What is the name of this compound? (Disubstituted methyl compound)

A

Ortho - Xylene (1,2-dimethylbenzene) (Ortho means 1,2)

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14
Q

What is the name of this compound? (Disubstituted methyl compound)

A

Meta - Xylene (1,3-dimethylbenzene) (Meta is 1,3)

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15
Q

What is the name of this compound? (Disubstituted methyl compound)

A

Para - Xylene (1,4-dimethylbenzene) (Para is 1,4)

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16
Q

Ortho, meta, & para can’t be used on aromatic ring that have _______ or more substituent

A

3 or more

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17
Q

When naming poly substituted benzene ring, we use the same method as naming alkanes but it’s common to use a ____________

A

Common name (Ex. 3,5,-dibromophenol)

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18
Q

What is the stabilization energy of benzene?

A

30 KJ/mol

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19
Q

What is the MO theory to explain the stability of Benzene?

A
  1. There are six molecular orbitals, each of which is associated with the entire molecule
  2. 3 of the 6 MOs are bonding MOs, while the other 3 MOs are antibonding MOs
  3. Since each MO can contain two electrons the 3 bonding MOs can collectively accommodate up to 6 pie electrons
  4. By occupying the bonding MOs, all 6 pie electron achieve a lower energy state & are said to be delocalized, which is the source of stabilization energy associated with benzene
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20
Q

What is Huckel’s Rule? (4n+2)

A

Need an odd number of electrons pairs for a compound to be aromatic (or have aromatic stabilization)

21
Q

What are the steps to the frost circle?

A
  1. Draw a circle
  2. Inscribe a polygon making sure one of the connecting points is at the bottom of the circle
  3. Draw a horizontal line at each pointof intersection
  4. Draw a dotted line through the center of the circle & earse the circle
  5. Identify all the bonding MOs & antibonding MOs (bonding MOs is below the line & antibonding MOs is above the line)
22
Q

What is the 2 criteria for a compound to be aromatic?

A
  1. The compound must obtain a ring comprised of continously overlapping p oribitals
  2. The number of pie electrons in the ring must be a huckel number

(If a compounds falls number 1 then its nonaromatic)

23
Q

Compounds that satisfy the 1st criterion but have 4n electrons rather than 4n+2 are what?

A

Antiaromatic

24
Q

Annulenes

A

Are compound consisting of a single containing a fully conjugated pie system

25
A ________ member ring will be aromatic if it contains 6 pie electrons
Five
26
For a 5 membered ring to have 6 electrons one of the carbon atoms must have 2 electrons (a carbanion) which the resulting anion is called \_\_\_\_\_\_\_\_\_\_\_\_\_\_\_
Cyclopentadienyl anion (has 5 resonance structures)
27
In order to have 6 electrons in a 7 membered ring one of the carbon atoms must have an empty p orbital (carbocation) which the resulting ion is called the \_\_\_\_\_\_\_\_\_\_\_
Tropylium Cation (has 7 resonance structures)
28
Heterocycles
Cyclic compounds containing heteroatoms such as S, N, or O
29
Huckel rules (4n+2) can only be applied to compounds that exhibit a _______ ring of overlapping p orbitals (Monosubstituted compounds)
Single
30
\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_ are stable (Have a fused benzene like rings)
Polycyclic Aromatic Hydrocarbons (PAHs) (ex. naphthalene)
31
Any carbon atom attached directly to a benzene ring is called what?
Benzylic position
32
When a alkyl benzene has one proton it can be oxidized with chromatic acid to produce \_\_\_\_\_\_\_\_\_\_
Benzoic Acid (only the benzylic position is oxidized)
33
Free-radical bromination occurs at the \_\_\_\_\_\_\_\_\_\_, the reaction is regioselective
Benzylic Position
34
Benzylic halides can undergo _________ & __________ reactions
Substitution & Elimination
35
What are the two ways to introduce a functional group at the benzylic position?
1. Oxidation to produce a benzoic acid 2. Radical Bromination to produce a benzylic halide that can undergo substitution & elimination reaction
36
Under forced conditions benzene will react with 3 equivalents of molecular hydrogen to produce \_\_\_\_\_\_\_\_\_\_\_\_\_
Cyclohexane
37
With some catalyst & under certain conditions its possible to hydrogenate a _________ group with an aromatic ring
Vinyl
38
Birch Reduction
States that benzene can be reduced with dissolving metal reduction (Na,CH3OH/NH3) to produce 1,4-cyclohexadiene
39
What is the mechanism for birch reduction?
1. Nucleophilic attack 2. Proton transfer 3. Nucleophilic attack 4. Proton transfer
40
When an alkyl benzene is treated with birch conditions the carbon atom connected to the alkyl group is not \_\_\_\_\_\_\_\_\_
Reduced
41
When an electron withdrawing group (like a carbonyl group) is used in a birch reaction then the position connected to the group is \_\_\_\_\_\_\_\_\_
Reduced
42
Aromatic compounds produces signals between _________ & _________ cm-1 in IR spectroscopy
1450 & 1600 cm-1
43
Signal between ____ & ____ ppm represents a proton in an aromatic ring where protons in the benzylic position produces signals at 2-3 ppm in an H NMR spectroscopy
6.5 & 8ppm
44
An integration of 5 is a ____________ & an integration of 4 is a ___________ in an H NMR spectroscopy
Monosubstituted ring, Disubstituted ring
45
The carbon of aromatic rings typically produces signal in the range of __________ ppm in a 13C spectrum
100-150ppm
46
For a ring to be aromatic and have a huckel rule what are the number of pie electrons it can have?
2,6,10,14,18 (4n+2)
47
What is the name of this structure?
Pyridine
48
What is the name of this structure?
Pyrrole

Organic Chemistry (47 decks)

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