Benzene Details

Question 1

How to predict Aromaticity:

Answer 1

1. is it cyclic w/ conjugated bonds 2. is each atom sp2 3. Is it planar 4. Huckel’s rule pass (pie- = 4n+2 is a positive integer)

Question 2

Interpret endo rule

Answer 2

EWG of dieneophile must be pointing down to be stable.

Question 3

How to interpret aromaticity test:

Answer 3

• Aromatic: passed all 4 tests - Anti-aromatic: failed 4 - Non-aromatic: fails 1,2 or 3

Question 4

What is an allotrope?

Answer 4

different forms of same element

Question 5

Common name: benzene w/ alcohol

Answer 5

phenol

Question 6

Common name: benzene w/ methyl

Answer 6

toluene

Question 7

Common name: benzene w/ ketone

Answer 7

acetophenone

Question 8

Common name: benzene with aldehyde

Answer 8

benzaldehyde

Question 9

Common name: benzene w/ carboxylic acid

Answer 9

benzoic acid

Question 10

Common name: benzene w/ NO2 group

Answer 10

nitrile benzene

Question 11

Benzene Naming: substituents at carbons 1 and 2

Answer 11

ortho

Question 12

Benzene Naming: substituents at carbons 1 and 3

Answer 12

meta

Question 13

Benzene Naming: substituents at carbons 1 and 4

Answer 13

para

Question 14

why is the benzylic position special?

Answer 14

it can form resonance stabilized cations and radicals. (think of breaking an H with fishhook arrows and moving the radical around the ring)