Module 3: Arenes and Aromaticity

a molecule is aromatic if?

when it is of a 4n+2 pi electron system, is cyclic, and fully conjugated (all carbons are sp² hybridized)

a molecule is nonaromatic if?

when it is fully conjugated, cyclic, of 4n pi electron system, more than 7 carbons

when is a molecule antiaromatic?

when it has a 4n pi electron system, is not fully conjugated (sp³ hybridized carbons present), has less than 7 carbon atoms.

when can an antiaromatic molecule conform to a nonaromatic molecule?

when the molecule has more than 7 carbon atoms.

Arene reactions: chlorination of toluene:

write the products for this reaction if there are 3 eq of Cl2

answer to previous card

Arene reactions: oxidation of alkylbenzenes

____ and ___, ____, ___ are the reagents used in the oxidation of alkylbenzenes

Na₂Cr₂O₇, and (H₂O, H₂SO₄, heat)

The oxidation of an alkylbenzene replaces the ___ chain (if there is a ___ present in benzylic position) with a ____ acid group

alkyl, (hydrogen), carboxylic

Arene reactions: Oxidation of alkylbenzenes

write the product for the following reaction:

answer to previous card:

oxidation of alkylbenzenes can only occur if there are ___ present

hydrogens

can this structure go through an oxidation reaction?

answer to previous card:

no, there are no hydrogens present in the R group

Reduction reactions of arenes: nitroarenes

A nitro group can be reduced to a ____ amine. One method is reduction with __ or __ in ___ and then treated with ___ as the second step

primary, Sn, Fe, HCl, NaOH

What is the product of this reaction

arene reduction reactions: Aryl Ketones

an aryl ketone carbonyl group can be reduced to an ___ group

alkyl

Clemmensen reduction uses ____ amalgam in conc. ___

Zn(Hg), HCl

what is the product of this reaction?

Wolff-Kishner reduction uses ___ and __ and __

hydrazine, KOH, and heat

Arene reactions: nucleophilic substitution in benzilic halides

what is the product of this reaction. What kind of reaction is it (sn1, sn2 or sn3 )?

Nomenclature:

what is the name of this molecule?

Pyridine

what is the name of this molecule?

Pyrrole

what is the name of this molecule?

Furan

what is the name of this molecule?

Thiophene

what is the name of this molecule?

Quinoline

what is the name of this molecule?

Isoquinoline

what is the name of this molecule?

Chlorobenzene

what is the name of this molecule?

ethyl benzene

what is the name of this molecule?

Toluene or Methylbenzene

what is the name of this molecule?

Phenol or Hydroxybenzene

what is the name of this molecule?

Aniline or Aminobenzene

what is the name of this molecule?

Benzoic acid

what is the name of this molecule?

Acetophenone

what is the name of this molecule?

Anisole or Methoxybenzene

what is the name of this molecule?

1,2-Dibromobenzene or o(ortho)-Dibromobenzene

what is the name of this molecule?

3-Bromotoluene or m(meta)-Bromotoluene

what is the name of this molecule?

4-Aminobenzoic acid or p(para)-Aminobenzoic acid

what is the name of this molecule? Hint: the ring is the substituent, not the alkyl chain

3-phenylpentane

what is the name of this molecule?

Benzylamine

what is the name of this molecule?

Biphenyl

what is the name of this molecule?

Naphthalene

what is the name of this molecule?

Anthracene

what is the name of this molecule?

Phenanthrene