18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the...
Transcript of 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the...
![Page 1: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/1.jpg)
• AROMATIC compounds or ARENES include
benzene and benzene derivatives.
– Aromatic compounds are quite common.
– Many aromatic compounds were originally isolated from
fragrant oils.
– However, many aromatic compounds are odorless.
18.1 Intro to Aromatic Compounds
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-1
![Page 2: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/2.jpg)
• 8 of the 10 best-selling drugs have aromatic
moieties.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-2
![Page 3: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/3.jpg)
• Coal contains aromatic rings fused together and
joined by nonromantic moieties.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-3
![Page 4: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/4.jpg)
• Benzene is generally the parent name for
monosubstituted derivatives.
18.2 Nomenclature of Benzene
Derivatives
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-4
![Page 5: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/5.jpg)
• Many benzene derivatives have common names
that become the parent name. (memorize these)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-5
![Page 6: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/6.jpg)
• If the substituent is larger than the ring, the
substituent becomes the parent chain.
• Aromatic rings are often represented with a Ph (for
phenyl) or with a φ (phi) symbol.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-6
![Page 7: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/7.jpg)
• The common name for dimethyl benzene
derivatives is XYLENE.
– What do ORTHO, META, and PARA mean?
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-7
![Page 8: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/8.jpg)
• Locants are required for rings with more than 2
substituents.
1. Identify the parent chain (generally the aromatic
ring):
– Often a common name can be the parent chain.
2. Identify and name the substituents.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-8
![Page 9: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/9.jpg)
3. Number the parent chain
– A substituent that is part of the parent
name must be assigned locant
NUMBER 1.
4. List the numbered substituents
before the parent name in
alphabetical order:
– Ignore prefixes (except iso) when
ordering alphabetically.
– Complete the name for the molecule
above.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-9
![Page 10: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/10.jpg)
Klein, Organic Chemistry 1e
Section: 18.2 What is the correct name for the following?
a. o-bromoaniline
b. 2-bromoaniline
c. 1-amino-2-bromobenzene
d. all of the above
NH2
Br
![Page 11: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/11.jpg)
• In 1866, August Kekulé proposed that benzene is
a ring comprised of alternating double and single
bonds.
– Kekulé suggested that the exchange of double and
single bonds was an equilibrium process.
18.3 Structure of Benzene
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-11
![Page 12: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/12.jpg)
• We now know that the aromatic structures are
resonance contributors rather than in equilibrium.
• Sometimes the ring is represented with a circle in
it
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-12
![Page 13: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/13.jpg)
• The stability that results from a ring being
aromatic is striking.
– Recall that in general, alkenes readily undergo addition
reactions.
– Aromatic rings are stable enough that they do not
undergo such reactions.
18.4 Stability of Benzene
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-13
![Page 14: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/14.jpg)
– Heats of hydrogenation can be used to quantify
aromatic stability.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-14
![Page 15: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/15.jpg)
• Molecular orbital (MO) theory can help us explain
aromatic stability.
• The six atomic p-orbitals of benzene overlap to
make six MOs.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-15
![Page 16: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/16.jpg)
Summary of Critical Points of MO Theory
• MO Theory is good for describing excited states,
ions, exotic species that defy Lewis structures.
• Mix n atomic orbitals to form n molecular orbitals
– each orbital has max occupation = 2 electrons
– Fill from lowest energy MO
– An MO has NO EFFECT until it contains an electron
– For each bonding MO, there exists an anti-bonding
MO that can exactly cancel the bonding MO
• Most likely excitation moves one electron from
HOMO to LUMO
![Page 17: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/17.jpg)
• we can use FROST CIRCLES to predict the
relative MO energies.
18.4 Stability of Benzene
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-17
![Page 18: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/18.jpg)
• Use the FROST CIRCLES below to explain the
4n+2 rule.
– Note that the number of bonding orbitals is always an
odd number; aromatic compounds will always have an
odd number of electron pairs.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-18
![Page 19: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/19.jpg)
• Some rings must carry a formal charge to be
aromatic.
• Consider a 5-membered ring.
18.5 Aromatic Compounds Other
Than Benzene
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-19
![Page 20: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/20.jpg)
• The pKa value for cyclopentadiene is much lower
than typical C-H bonds. WHY?
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-20
vs.
![Page 21: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/21.jpg)
• Consider a 7-membered ring.
– If six pi electrons are present, what charge will be
necessary?
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-21
![Page 22: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/22.jpg)
Klein, Organic Chemistry 1e
Which of the following are aromatic?
A. B. C.
a. A
b. B
c. C
d. A and B
e. B and C
f. A and C
g. none of the above
h. all of the above
![Page 23: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/23.jpg)
• Heteroatoms (atoms other than C or H) can also
be part of an aromatic ring.
– If the heteroatom’s lone pair is necessary, it will be
included in the HÜCKEL number of pi electrons.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-23
![Page 24: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/24.jpg)
• If the lone pair is necessary to make it aromatic,
the electrons will not be as basic.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-24
pKa=5.2
pKa=0.4
![Page 25: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/25.jpg)
• The difference in electron density can also be
observed by viewing the electrostatic potential
maps.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-25
![Page 26: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/26.jpg)
• Will the compounds below be aromatic,
antiaromatic, or non aromatic?
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-26
![Page 27: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/27.jpg)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-27
![Page 28: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/28.jpg)
• A carbon that is attached to a benzene
ring is BENZYLIC.
• Recall that aromatic rings and alkyl
groups are not easily oxidized.
18.6 Reactions at the Benzylic
Position
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-28
![Page 29: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/29.jpg)
• HOWEVER, benzylic positions can readily be fully
oxidized.
– The benzylic position needs to have at least one proton
attached to undergo oxidation.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-29
![Page 30: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/30.jpg)
• Permanganate can also be used as an oxidizing
reagent.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-30
![Page 31: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/31.jpg)
• BENZYLIC positions have similar
reactivity to allylic positions.
– Benzylic positions readily undergo free radical
bromination.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-31
![Page 32: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/32.jpg)
• Once the benzylic position is substituted with a
bromine atom, a range of functional group
transformations are possible.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-32
![Page 33: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/33.jpg)
• Once the benzylic position is substituted with a
bromine atom, a range of functional group
transformations are possible.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-33
![Page 34: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/34.jpg)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-34
![Page 35: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/35.jpg)
• Give necessary reagents for the reactions below.
18.6 Reactions at the Benzylic
Position
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-35
![Page 36: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/36.jpg)
Klein, Organic Chemistry 1e
Section: 18.6 What is the correct order of reagents to
achieve the following synthesis?
a. 1) CH3CH2CH2MgBr 2) H2O
b. NBS, light, CCl4
c. HBr
d. NaBr
e. 1) LAH 2) H2O
O Br
1) A
2) E, B
3) E, C
4) E, D
5) E, B, C
![Page 37: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/37.jpg)
• Under forceful conditions, benzene can be
reduced to cyclohexane.
– Is the process endothermic or exothermic? WHY?
– WHY are forceful conditions required?
18.7 Reduction of the Aromatic
Moiety
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-37
![Page 38: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/38.jpg)
• Vinyl side groups can be selectively reduced.
– ΔH is just slightly less than the expected –120 kJ/mol
expected for a C=C C–C conversion.
– WHY are less forceful conditions required?
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-38
![Page 39: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/39.jpg)
• Note that the BIRCH reduction product has sp3
hybridized carbons on opposite ends of the ring.
18.7 Reduction of the Aromatic
Moiety
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-39
![Page 40: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/40.jpg)
• Like alkenes, benzene can undergo the BIRCH
reduction.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-40
![Page 41: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/41.jpg)
• Like alkenes, benzene can undergo the BIRCH
reduction.
– Draw the final product.
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-41
![Page 42: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/42.jpg)
– The presence of an electron donating alkyl side group
or EWD groups provides different regioselectivity. Why?
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-42
![Page 43: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/43.jpg)
Klein, Organic Chemistry 1e
Section: 18.7 What is the product(s) of the following
reaction.
A. C.
B. D.
NO2
Na, CH3OH NH3
NO2
NO2
NO2
NO2
![Page 44: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/44.jpg)
Klein, Organic Chemistry 1e
Section: 18.8
In 1H NMR spectrometry, aromatic C-H bonds show peaks
at _______ ppm.
In C NMR spectrometry, aromatic carbons show peaks at
_______ ppm.
In IR spectroscopy, aromatic C-H bonds show peaks at
_______ cm–1.
a. 3–4, 100–150, 1450–1600
b. 6.5-8.5, 100–150, 3000-3100
c. 3–4, 100–150, 2250
d. 6.5-8.5, 100–150, 1450–1600
![Page 45: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/45.jpg)
18.8 Spectroscopy of Aromatic
Compounds
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-45
![Page 46: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/46.jpg)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-46
• IR spectra for ethylbenzene:
![Page 47: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/47.jpg)
NMR of Aromatics
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-47
– Recall from Section 16.5 how the anisotropic
effects of an aromatic ring affect NMR shifts.
![Page 48: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/48.jpg)
NMR of Aromatics
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-48
– The integration and splitting of protons in the
aromatic region of the 1H NMR (≈7 ppm) in
often very useful.
![Page 49: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/49.jpg)
NMR of Aromatic Compounds
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-49
– Because of possible ring symmetry, the number
of signals in the 13C NMR (≈100-150 ppm)
generally provides structural information.
![Page 50: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/50.jpg)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-50
– For the molecule below, predict the shift for the 13C signals, and predict the shift, integration,
and multiplicity for the 1H NMR signals.
![Page 51: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/51.jpg)
Graphite, Buckyballs, and
Nanotubes
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-51
• Graphite consists of layers of sheets of
fused aromatic rings.
![Page 52: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/52.jpg)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-52
• Buckyballs are C60 spheres made of
interlocking aromatic rings.
– Fullerenes come in other sizes such as C70.
– How are Buckyballs aromatic when they are not
FLAT?
![Page 53: 18.1 Intro to Aromatic Compounds - Organic … Organic Chemistry 1e Section: 18.2 What is the correct name for the following? a. o-bromoaniline b. 2-bromoaniline c. 1-amino-2-bromobenzene](https://reader031.fdocuments.us/reader031/viewer/2022030822/5b377cd27f8b9a5a518c6b59/html5/thumbnails/53.jpg)
Copyright 2012 John
Wiley & Sons, Inc.
Klein, Organic Chemistry 1e 18-53
• Fullerenes can also be made into tubes
(cylinders).
• Single, double, and multi-walled carbon nanotubes
have many applications:
– Conductive Plastics, Energy Storage, Conductive
Adhesives, Molecular Electronics, Thermal Materials,
Fibres and Fabrics, Catalyst Supports, Biomedical
Applications