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Organic Chemistry > Organic Test 5 > Flashcards

Organic Test 5 Flashcards

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1
Q

What is the polygon rule?

A

You can form a polygon with a conjugated ring to determine stability and number of bonding, nonbonding, and antibonding electrons

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2
Q

What is the mechanism for the formation of a stronger electrophile in the bromination of benzene?

A
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3
Q

What is the name of this functional group?

A

acetophenone

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4
Q

Name? position?

A

o-dichlorobenzene

1,2-dichlorobenzene

(ortho)

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5
Q

The sulfonation reaction is reversible by using either concentrated/dilute sulfuric acid. Which is which?

A
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6
Q

What is the name of this group?

A

acetyl

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7
Q

What kind of directors are anisole groups?

A

STRONG activators, so they are:

ortho para directors.

They ortho and para positions are stabilized by resonance

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8
Q

What kind of directors are alkyl groups?

A

They are activators, so they are:

ortho-para directors

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9
Q

What are all of the ortho-para, activator groups?

A

Aka alkylbenzenes and groups with lone pairs to stabilize resonance forms.

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10
Q

What kind of director are halogens?

A

They are deactivating BUT ortho-para directors

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11
Q

What is the difference between the phenyl and benzyl groups?

A
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12
Q

What is the name of this functional group?

A

benzaldehyde

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13
Q

If two groups donate, what is more important, resonance or induction?

A

Resonance is more important.

Fyi, CH3 donates by induction

Cl donates by resonance

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14
Q
A
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15
Q

Name?

A

benzoic acid

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16
Q

Name?

A

anisole

(methoxybenzene)

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17
Q

What kind of directors are ketones and aldehydes?

A

meta-directors, deactivators

18
Q

What kind of director is sulfonic acid?

A

Meta-director, deactivator

19
Q

When both meta directors and O/P directors are present, which wins?

A

O/P

20
Q

In Birch reduction of substituted benzenes, how do we know where the 1,4 diene goes?

A

deactivators: are reduced
activators: are NOT reduced

21
Q

What kind of directors are esters?

A

Meta-directors, deactivators

22
Q

name?

A

styrene

(vinylbenzene)

23
Q

What are 2 limitations of the friedel-crafts reaction?

A
  1. Friedel-crafts reactions work only with benzene, activated benzene derivatives, and halobenzenes.

Does not work with:

  • deactivating group stronger than a halogen (NO2, SO3H, CO2H, CN, R-C=O, H-C=O, +NR3, -O-R-C=O)
  • Lewis acid-base adduct formed from amino groupsm (NH2, NHR, NR2)
    2. susceptible to carbocation rearrangement, therefore you can’t make straight chain alkanes.
24
Q

What kind of director is the nitro group?

A

Deactivator,

Meta-director

25
Q

What kind of director is the cyano group?

A

meta-director, deactivator

26
Q

What kind of directors are aniline groups?

A

Aniline groups are activators

they are ortho para directors due to resonance stabilized ortho and para positions.

27
Q

What is necessary for compounds to be aromatic?

A
  1. The structure must be cyclic and contain conjugated pi bonds
  2. Each atom must have an unhybridized p orbital (sp2 or sp)
  3. The unhybridized p orbitals must overlap to form a continuous ring of parallel orbitals. Must be planar for effective overlap
28
Q

what is the name of this group?

A

acyl group

29
Q

What kind of director is quartenary ammonium?

A

Meta-director, deactivator

30
Q

Name?

A

toluene

(methylbenzene)

31
Q

Name?

A

aniline

(benzenamine)

32
Q

What is the preliminary step to form the strong electrophile needed in the nitration of benzene?

A
33
Q

name?

A

phenol

(benzenol)

34
Q

What is the connection between the number of conjugated double bonds and UV absorption?

A

A compound that has a longer chain of conjugated double bonds, absorbs UV at a HIGHER wavelength

35
Q

Name? Position?

A

p-nitrophenol

IUPAC: 4-nitrophenol

(para)

36
Q

Name?

A

acetophenone

(methyl phenyl ketone)

37
Q

Name?

A

benzaldehyde

38
Q

What is the best way to add an amino group to an aromatic ring?

A

Starting with a nitro group is the best way to get an amino group with a metal catalyst.

39
Q

What is the mechanism for electrophilic aromatic substitution?

A
40
Q

If a conjugated system meets the three rules of aromaticity, how do you determine if it is aromatic or antiaromatic?

A

aromatic: 4N+2 rule
antiaromatic: 4N rule

where n is the number of pi electrons

41
Q

What is the name of this functional group?

A

anisole

42
Q

Name? Position?

A

m-chloroperoxybenzoic acid

IUPAC: 3-chloroperoxybenzoic acid

(meta)

Organic Chemistry (8 decks)

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