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GAMSAT Chemistry organic reaction pathways > 5. Aromatic Compounds > Flashcards

5. Aromatic Compounds Flashcards

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1
Q

where does resonance come from in a aromatic compound

A

from the conjugated double bonds in the benzene

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2
Q

how many pi bonds are in an aromatic compound

A

4N + 2

N = whole number of rings

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3
Q

what is ortho nomenclature

A

2 attachments next to each other on the ring

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4
Q

what is meta nomenclature

A

2 attachments on ring with one space between the 2

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5
Q

what is para nomenclature

A

2 attachments on ring opposite each other

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6
Q

how is a mono/di-substituted aromatic compound prepared

A

electrophillic aromatic substitution

addition of E+ followed by elimination of H

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7
Q

what influences where the substituent goes when preparing a disubstituted aromatic compound

A

the first substituent on the ring controls whether the incoming electrophile is ortho/meta/para position

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8
Q

what kinds of activating and halogen deactivating substituents on the ring are ortho/para directing

A

strong/weak activating and deactivating

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9
Q

what is an example of a strongly activating substituent

A

-OH
-OR

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10
Q

what is an example of a weakly activating substituent

A

-CH3

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11
Q

what is an example of a deactivating substituent

A

-X

eg -F/Br/Cl/I

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12
Q

what do activating groups do to the e- density

A

pushes it into the ring

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13
Q

what do deactivating groups do to the e- density

A

pulls it out of the ring

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14
Q

why is ortho/para more liekly to occur than meta

A

o/p has 4 resonance structures while meta only has 3 so o/p more likely to occur

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15
Q

what kinds of activating/deactivating substituents on the ring are meta directing

A

strong/moderate deactivating

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16
Q

what are examples of strongly deactivating substituents

A

-NO-

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17
Q

what are examples of moderate deactivating substituents

A

-COH

-COR

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18
Q

what reagents or reactants are needed for an aromatic compound (benzene ring)
when it undergoes friedel crafts acylation

A

RXC=O + AlX3

(R & X attached to the C)

19
Q

what is produced when an aromatic compound (benzene ring) undergoes friedel crafts acylation

A

adds RC=O onto aromatic ring

20
Q

what is produced when RXC=O is added to AlX3 for aromatic compounds (benzene ring)

(R & X attached to the C)

A

produces aromatic ring with RC=O substituent

21
Q

what reagents or reactants are needed for an aromatic compound (benzene ring)
when it undergoes friedel crafts alkylation

A

RX + AlX3

22
Q

for what types of alkanes can friedel crafts alkylation occur

A

small alkanes

23
Q

what is produced when RX is added to AlX3 for aromatic compounds (benzene ring)

A

friedel crafts alkylation

produces aromatic ring with R attached

24
Q

what kind of substitution are friedels craft acylation/alkylation

A

mono substitution

25
Q

how do you go from a benzene ring no substituents to a X as the only substituent on the benzene ring

what reagents or reactants are needed

A

+X2/FeX3

where X = Cl or Br

26
Q

how do you go from a benzene ring no substituents to a RC=O as the only substituent on the benzene ring

what reagents or reactants are needed

A

+RXC=O/AlX3

(R & X attached to the C)

27
Q

how do you go from a benzene ring no substituents to a CH3 as the only substituent on the benzene ring

what reagents or reactants are needed

A

+CH3X/AlX3

28
Q

how do you go from a benzene ring no substituents to a NO2 as the only substituent on the benzene ring

what reagents or reactants are needed

A

+HNO3/H2SO4

29
Q

what happens when you

+RXC=O/AlX3

to a non substituted benzene ring (what is produced)

A

-RC=O added onto the ring

30
Q

what happens when you

+X2/FeX3

to a non substituted benzene ring

A

-X added onto the ring

31
Q

what happens when you

+CH3X/AlX3

to a non substituted benzene ring

A

-CH3 added onto the ring

32
Q

what happens when you

+HNO3/H2SO4

to a non substituted benzene ring

A

-NO2 added onto the ring

33
Q

how do you go from a benzene ring with -NO2 attached as the only substituent on the benzene ring to a -NH2 as the only substituent on the benzene ring

what reagents or reactants are needed

A

+Fe/H+ & OH-

34
Q

how do you go from a benzene ring with -NH2 attached as the only substituent on the benzene ring to a -N(triple bond)N as the only substituent on the benzene ring

what reagents or reactants are needed

A

+HNO2/0 degrees celsius

35
Q

how do you go from a benzene ring with -N(triple bond)N attached as the only substituent on the benzene ring to a -OH as the only substituent on the benzene ring

what reagents or reactants are needed

A

+H3O+

36
Q

how do you go from a benzene ring with –N(triple bond)N attached as the only substituent on the benzene ring to a -CN as the only substituent on the benzene ring

what reagents or reactants are needed

A

+CuCN

37
Q

how do you go from a benzene ring with -CN attached as the only substituent on the benzene ring to a -COOH as the only substituent on the benzene ring

what reagents or reactants are needed

A

+H3O+

38
Q

how do you go from a benzene ring with -COOH attached as the only substituent on the benzene ring to a -ClC=O as the only substituent on the benzene ring

what reagents or reactants are needed

A

+SOCl2

39
Q

what happens when you

+Fe/H+ & OH-

to a benzene ring with a -NO2 attached

A

-NH2 replaces the -NO2

40
Q

what happens when you

+HNO2/0 degrees celsius

to a benzene ring with a -NH2 attached

A

-N(triple bond)N replaces the -NH2

41
Q

what happens when you

+H3O+

to a benzene ring with a -N(triple bond)N attached

A

-OH replaces the -N(triple bond)N

42
Q

what happens when you

+CuCN

to a benzene ring with a -N(triple bond)N attached

A

-CN replaces the -N(triple bond)N

43
Q

what happens when you

+H3O+

to a benzene ring with a -CN attached

A

-COOH replaces the -CN

44
Q

what happens when you

+SOCl2

to a benzene ring with a -OH attached

A

-ClC=O replaces the -COOH

GAMSAT Chemistry organic reaction pathways (12 decks)

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