Exam 1

Question 1

Styrene

Answer 1

benzene with a C=C attached

Question 2

Toluene

Answer 2

benzene with methyl attached

Question 3

Phenol

Answer 3

benzene with an alcohol attached

Question 4

Aniline

Answer 4

benzene with NH2 attached

Question 4

Anisole

Answer 4

benzene with OCH3 attached

Question 5

Acetophenone

Answer 5

benzene with acetone attached

Question 6

Benzaldenyde

Answer 6

benzene with an aldehyde attached

Question 7

Benzoic acid

Answer 7

benzene with a carboxylic acid attached

Question 8

Meta-xylene

Answer 8

benzene with 2 methyl groups attached with a carbon between them

Question 9

Para-xylene

Answer 9

benzene with 2 methyl groups attached 180 degrees apart from each other

Question 10

EWG

Answer 10

-Electron withdrawing group
-destabilizes carbocation and slows down EAS reaction

Question 11

EDG

Answer 11

-Electron donating group
-Stabilizes carbocation and speeds up EAS reaction
-Usually has an oxygen or nitrogen with a filled electron shell
-The lower electronegativity, the more readily the atom is to give up its electrons

Question 12

EDG or halogen as a substituent

Answer 12

ortho and para

Question 13

EWG substituent

Answer 13

meta

Question 14

Rate of Diels-Alder reactions

Answer 14

-Increases with increasing number of EWGs on dienophile
-In order for the reaction to proceed, the diene must be able to access the s-cis conformation

Question 15

How to determine aromaticity

Answer 15

1. molecule must be flat
2. all atoms in the ring are sp2
   If neither are true then the molecule is nonaromatic
   If both are true then
3. If the number of pi electrons is 4n then the molecule is antiaromatic
   If the number of pi electrons is 4n+2 then the molecule is aromatic
   If a frost cycle is made and orbitals are filled then the molecule is aromatic but if there are partially filled orbitals then it’s antiaromatic
   If the number of pi electrons divided by 2 is odd then it’s aromatic but if it’s even then it’s antiaromatic

Question 16

Bromination electrophile

Answer 16

Br+

Question 17

Nitration electrophile

Answer 17

NO2+

Question 18

Friedel-Craft Alkylation electrophile

Answer 18

R+

Question 19

Friedel-Craft Acylation electrophile

Answer 19

R-C+
||
O

Question 20

Sulfonation electrophile

Answer 20

HSO3+

Question 21

Bromination mechanism

Answer 21

draw

Question 22

Nitration mechanism

Answer 22

draw

Question 23

FC Alkylation mechanism

Answer 23

draw

Question 24

FC Acylation mechanism

Answer 24

draw

Question 25

Sulfonation mechanism

Answer 25

draw

Question 26

EAS Reaction mechanism

Answer 26

draw

Question 27

Para

Answer 27

substituents are 180 degrees apart

Question 28

Ortho

Answer 28

substituents are right next to each other

Question 29

Meta

Answer 29

substituents are attached with a space between them

Question 30

Kinetic products

Answer 30

-require less energy -formed faster than thermodynamic product -will be above thermodynamic product

Question 31

Thermodynamic products

Answer 31

-require more energy to make -will be below kinetic product -more stable than kinetic products

Question 32

Bromination catalysts

Answer 32

Br2 and FeBr3

Question 33

Nitration catalysts

Answer 33

HNO3 and H2SO4

Question 34

Sulfonation catalysts

Answer 34

SO3 and H2SO4

Question 35

FC Acylation catalysts

Answer 35

carbon with an attached chlorine R group, and double bonded oxygen and AlCl3

Question 36

FC Alkylation catalysts

Answer 36

sp2 or sp3 alkyl halide and AlCl3