Chapter 11: Aromatic Compouds

What is the first rule when determining if a compound is aromatic?

It must me cyclic or polycyclic

What is the second rule in determining if a compound is aromatic?

All the atoms must be sp² or sp hybridized

What is the third rule in determining if a compound is aromatic?

It must follow Hückel’s rule: the number of pi electrons in a compound must equal 4n+2

What is the fourth rule in determining if a compound is aromatic?

The compound must be planar

If the compound does not meet rule 1,2 or 4 what is it called?

Non-aromatic

If the compound meets rule and 2 but not 3 what is it called?

Anti-aromatic

What reaction conditions can convert a benzylic carbon with at least one H to carboxylic acid (making the whole structure a benzoic acid?)

Either:

1)KMnO₄, OH- 2)H₃O⁺, heat

or

Na₂Cr₂O₇/H₂SO₄

What is the needed for a reactant to work for Clemmensen reduction?

Aldehyde or Ketone

What is the reagent for a Celmmensen reduction?

Zn(Hg), HCl, heat

What happens in a Clemmensen reduction?

The carbonyl group of a ketone or aldehyde is converted into CH₂

True or false: Wolff-Kishner Reduction occurs the same way Clemmensen reduction does, with the same products

True

What is the reagent used in Wolff-Kishner reductions?

H₂NNH₂, HO-, heat

What reagent adds NO₂ to a benzene? (EAS)

HNO₃,H₂SO₄

What reagent adds SO₃H to a benzene? (EAS)

SO₃, H₂SO₄

What reagent adds a Cl to a benzene? (EAS)

Cl₂, AlCl₃(catalyst)

What reagent adds a Br to a benzene? (EAS)

Br₂, FeBr₃(catalyst)

What is Friedel-Crafts Alkylation?(EAS)

Adding an R group to a benzene

What is the Friedel-Crafts Alkylation reagent?

R-Cl, AlCl₃

What is Friedel-Crafts Acylation?(EAS)

The addition of a ketone to a benenze

What is the reagent required for Friedel-Crafts Acylation?

ClCOR, AlCl₃

What is Formylation?(EAS)

Adding a aldehyde to a benzene

What is the reagent used for formylation?

CO,HCl,AlCl₃,CuCl

If the benzene starts with a substituent what is the first step (EAS)

Determine if the substituent is a ortha/para director or a meta director

What is a meta director

an electron withdrawer. Many have double or triple bonds(including alkenes and alkynes). a NR₃⁺ is also a meta director

What are ortho/para directors

Electron donors

Why are the ortho/para positions favored for electron donors and the meta position for electron withdrawers?

This is due to the resonance that occurs

What is the process of going from a benzene to a phenol?

[1] add NO₂ to the benzene [2] convert the NO₂ to an aniline (NH₂) [3] convert the aniline to a diazonium salt(N₂⁺) [4] convert the diazonium salt to an alcohol (OH)

What reagents can be used to convert NO₂ to NH₂?

H₂, Pd/C or Sn, HCl

What reagents convert aniline to diazonium salt?

NaNO₂, HCL (HONO)

What reagents convert a benzene diazonium salt to a phenol?

H₃O⁺ or EtOH

What reagents convert a benzene diazonium salt to a benzene Br or Cl?

CuBr or CuCl

What reagents convert a benzene diazonium salt to a benzene nitrile (C tripple bonded to N)

CuCN

What reagents convert a benzene diazonium salt to a benzene iodine?

KI

What reagents convert a benzene diazonium salt to a benzene Floride?

HBF₄

What reagents convert a benzene diazonium salt to a benzene

H₃PO₂

What reagents are weak O/P directors?

the 4 first halogens

What are strong O/P directors

NH₂,OR/H,R,benzene, (if it has extra electrons or is negative)

What to do if there are multiple substituents? (EAS)

If there is a strong O/P follow it, then weak then finally meta directors

What type of director causes Friedel crafts reactions to not work?

Meta directors unless canceled out by an O/P