Organic Test 5

Question 1

What is the polygon rule?

Answer 1

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

Question 2

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

Answer 2

Question 3

What is the name of this functional group?

Answer 3

acetophenone

Question 4

Name? position?

Answer 4

o-dichlorobenzene

1,2-dichlorobenzene

(ortho)

Question 5

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

Answer 5

Question 6

What is the name of this group?

Answer 6

acetyl

Question 7

What kind of directors are anisole groups?

Answer 7

STRONG activators, so they are:

ortho para directors.

They ortho and para positions are stabilized by resonance

Question 8

What kind of directors are alkyl groups?

Answer 8

They are activators, so they are:

ortho-para directors

Question 9

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

Answer 9

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

Question 10

What kind of director are halogens?

Answer 10

They are deactivating BUT ortho-para directors

Question 11

What is the difference between the phenyl and benzyl groups?

Answer 11

Question 12

What is the name of this functional group?

Answer 12

benzaldehyde

Question 13

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

Answer 13

Resonance is more important.

Fyi, CH3 donates by induction

Cl donates by resonance

Question 15

Name?

Answer 15

benzoic acid

Question 16

Name?

Answer 16

anisole

(methoxybenzene)

Question 17

What kind of directors are ketones and aldehydes?

Answer 17

meta-directors, deactivators

Question 18

What kind of director is sulfonic acid?

Answer 18

Meta-director, deactivator

Question 19

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

Answer 19

O/P

Question 20

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

Answer 20

deactivators: are reduced
activators: are NOT reduced

Question 21

What kind of directors are esters?

Answer 21

Meta-directors, deactivators

Question 22

name?

Answer 22

styrene

(vinylbenzene)

Question 23

What are 2 limitations of the friedel-crafts reaction?

Answer 23

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.

Question 24

What kind of director is the nitro group?

Answer 24

Deactivator,

Meta-director

Question 25

What kind of director is the cyano group?

Answer 25

meta-director, deactivator

Question 26

What kind of directors are aniline groups?

Answer 26

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

Question 27

What is necessary for compounds to be aromatic?

Answer 27

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

Question 28

what is the name of this group?

Answer 28

acyl group

Question 29

What kind of director is quartenary ammonium?

Answer 29

Meta-director, deactivator

Question 30

Name?

Answer 30

toluene | (methylbenzene)

Question 31

Name?

Answer 31

aniline | (benzenamine)

Question 32

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

Answer 32

Question 33

name?

Answer 33

phenol | (benzenol)

Question 34

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

Answer 34

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

Question 35

Name? Position?

Answer 35

p-nitrophenol IUPAC: 4-nitrophenol (para)

Question 36

Name?

Answer 36

acetophenone | (methyl phenyl ketone)

Question 37

Name?

Answer 37

benzaldehyde

Question 38

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

Answer 38

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

Question 39

What is the mechanism for electrophilic aromatic substitution?

Answer 39

Question 40

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

Answer 40

aromatic: 4N+2 rule antiaromatic: 4N rule where n is the number of pi electrons

Question 41

What is the name of this functional group?

Answer 41

anisole

Question 42

Name? Position?

Answer 42

m-chloroperoxybenzoic acid IUPAC: 3-chloroperoxybenzoic acid (meta)