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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
Q

A ________ member ring will be aromatic if it contains 6 pie electrons

26
Q

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 _______________

A

Cyclopentadienyl anion (has 5 resonance structures)

27
Q

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 ___________

A

Tropylium Cation (has 7 resonance structures)

28
Q

Heterocycles

A

Cyclic compounds containing heteroatoms such as S, N, or O

29
Q

Huckel rules (4n+2) can only be applied to compounds that exhibit a _______ ring of overlapping p orbitals (Monosubstituted compounds)

30
Q

_______________ are stable (Have a fused benzene like rings)

A

Polycyclic Aromatic Hydrocarbons (PAHs) (ex. naphthalene)

31
Q

Any carbon atom attached directly to a benzene ring is called what?

A

Benzylic position

32
Q

When a alkyl benzene has one proton it can be oxidized with chromatic acid to produce __________

A

Benzoic Acid (only the benzylic position is oxidized)

33
Q

Free-radical bromination occurs at the __________, the reaction is regioselective

A

Benzylic Position

34
Q

Benzylic halides can undergo _________ & __________ reactions

A

Substitution & Elimination

35
Q

What are the two ways to introduce a functional group at the benzylic position?

A
  1. Oxidation to produce a benzoic acid
  2. Radical Bromination to produce a benzylic halide that can undergo substitution & elimination reaction
36
Q

Under forced conditions benzene will react with 3 equivalents of molecular hydrogen to produce _____________

A

Cyclohexane

37
Q

With some catalyst & under certain conditions its possible to hydrogenate a _________ group with an aromatic ring

38
Q

Birch Reduction

A

States that benzene can be reduced with dissolving metal reduction (Na,CH3OH/NH3) to produce 1,4-cyclohexadiene

39
Q

What is the mechanism for birch reduction?

A
  1. Nucleophilic attack
  2. Proton transfer
  3. Nucleophilic attack
  4. Proton transfer
40
Q

When an alkyl benzene is treated with birch conditions the carbon atom connected to the alkyl group is not _________

41
Q

When an electron withdrawing group (like a carbonyl group) is used in a birch reaction then the position connected to the group is _________

42
Q

Aromatic compounds produces signals between _________ & _________ cm-1 in IR spectroscopy

A

1450 & 1600 cm-1

43
Q

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

A

6.5 & 8ppm

44
Q

An integration of 5 is a ____________ & an integration of 4 is a ___________ in an H NMR spectroscopy

A

Monosubstituted ring, Disubstituted ring

45
Q

The carbon of aromatic rings typically produces signal in the range of __________ ppm in a 13C spectrum

A

100-150ppm

46
Q

For a ring to be aromatic and have a huckel rule what are the number of pie electrons it can have?

A

2,6,10,14,18 (4n+2)

47
Q

What is the name of this structure?

48
Q

What is the name of this structure?

Organic Chemistry (47 decks)

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