exam #2

Question 1

Aromaticity

Answer 1

• cynic
• planar
• conjugated pi bonds

Question 2

CH3 Group

Answer 2

Common: toluene
IUPAC: methyl benzene

Question 3

OH Group

Answer 3

Common: Phenol
IUPAC: Benzenol

Question 4

OCH3 Group

Answer 4

Common: Anisole
IUPAC: methoxy-benzene

Question 5

NH2 Group

Answer 5

Common: Aniline
IUPAC: benzenamine

Question 6

CH=CH2

Answer 6

Common: Styrene
IUPAC: vinyl benzene

Question 7

CH=O

Answer 7

Common: benzaldehyde
IUPAC: benzene carbadlehyde

Question 8

O=C-O-H

Answer 8

Common: benzoic acid

Benzene Carboxcylic Acid

Question 9

Two substituents:

Answer 9

• add their position (ortho, meta, para, etc)
• make sure the first ends in O
• always do alphabetical
• always label the number position
• remember tri/di

Question 10

FeCL creates

Answer 10

Cl

good electrophile

Question 11

HNO3
———>
H2SO4

Answer 11

NO2

Question 12

SO3
——>
H2SO4

Answer 12

SO3H

Question 13

ALCl3

Answer 13

adds an R group

Question 14

Deactivating

Answer 14

Meta director

Question 15

Activating

Answer 15

ortho/para

Question 16

When do you reverse S/R configuration

Answer 16

if the smallest group is on a wedge instead of a dash.

Question 17

what does no enantiomers mean

Answer 17

MESO

Question 18

SN2

Answer 18

CH3-BR –> CH3-OH +Br

• primary carbons 1>2>3
• weaker the base the better
• wants a strong not bulky nucleophile
• CH3O is an example of one

Question 19

E2

Answer 19

CH3CH2CH2Br + Oh –> CH3CH=CH2 + H2O + Br

• likes primary carbons
• double bonds
• Likes OH as a nucleophile
• strong nucleophile
• opposite of SN2 where it is 3>2>1

Question 20

E1

Answer 20

• wants greatest number of R groups for nucleophile
  -weak nucleophile, very bulky.
  3>2>1
• double bonds

Question 21

SN1

Answer 21

• weak nucleophile (bulky) (H2O, ROH, COOH)

- 3>2>1

Question 22

substitution reaction

Answer 22

major product = one with most hydrogens

Question 23

elimination reactions

Answer 23

major product = one with fewest number of hydrogens

Question 24

what is a racemic mixture

Answer 24

50:50 mixture of enantiomers

Question 25

What makes a good nucleophile?

Answer 25

• small (unhindered)

- negatively charged

Question 26

ortho

Answer 26

1, 2

Question 27

meta

Answer 27

1, 3

Question 28

para

Answer 28

1, 4

- major

Question 29

what position are halogens always?

Answer 29

• ortho/para, but when doing it out you put into meta position (see problem 4)

Question 30

how do you find the enantiomer pair number

Answer 30

half of he number of stereoisomers (2^N)

Question 31

Enantiomers

Answer 31

• mirror images of each other

Question 32

disteriomers

Answer 32

• they do not mirror each other

Question 33

What do mirror planes mean?

Answer 33

• meso compound

- optically inactive

Question 34

(CH3)3 CCl + (CH3)3CO Na is under which pathway

Answer 34

• E2
• Cl and Na is strong nucleophile
• Cl is replaced by the strong base of Na
• O is strictly neutral
• tertiary carbon
• bulky = strong base

Question 35

where do you break the double bond in a resonance structure

Answer 35

where the electrophile is added

Question 36

what does it mean when there is a mirror plane

Answer 36

it is a meso compound

Question 37

the slowest step of an SN1 reaction involves

Answer 37

breaking the bond between carbon and the leaving groups to give a carbocation

Question 38

in what reaction does the displacement occur with inversion of configuration

Answer 38

SN2

Question 39

what is the beat leave in group

Answer 39

I
- weak bases
I

Question 40

what is an example of a strong base

Answer 40

NH2