Intro to Organic Chem

Question 1

Common Valences: H,C,N,O,F,S,P,Si,Cl

Answer 1

H=0,C=4,N=3,O=2,F=1,S=1,P=5,Si=4,Cl=1

Question 2

Formal Charge

Answer 2

FC=# valence e- - #bonds - # non-bonding e-

Question 3

VESPER Orbitals: sp,sp2,sp3,sp3d,sp3,d2

Answer 3

sp: 180°, linear
sp2: 120°, Trigonal Planar
sp3: 109.5°, Tetrahedral, pyramidal
sp3d: 90°, 120°, Trigonal-bi pyramidal, see-saw, t-shaped, linear
sp3d2: 90°,90°, octahedral, square pyramidal, square planar

Question 4

Huckel’s Rule (resonance)

Answer 4

4n+2 pi-electrons

Question 5

Nucleophile

Answer 5

δ-, attacks δ+, donate e-, lewis base

Question 6

Electropile

Answer 6

δ+, attacks δ-, accept e-, lewis acid

Question 7

Alkane

Answer 7

C-C

Question 8

Alkene

Answer 8

C=C

Question 9

Alkyne

Answer 9

C-(3)-C

Question 10

Alcohol

Answer 10

R-OH

Question 11

Ether

Answer 11

R-O-R’

Question 12

Amine

Answer 12

R-N-H R-N-H R-N-R’
| | |
H R’ R’’

Question 13

Aldehyde

Answer 13

O
||
R-C-H

Question 14

Ketone

Answer 14

O
||
R-C-R’

Question 15

Carboxylic Acid

Answer 15

O
||
R-C-OH

Question 16

Ester

Answer 16

O
||
R-C-O-R’

Question 17

Amide

Answer 17

O
||
R-C-NH2

Question 18

Alkyl

Answer 18

C-C-X

Question 19

Gem-dihalide

Answer 19

C-C-X
|
X

Question 20

Vic-Dihalide

Answer 20

C-C-X
| |
X X

Question 21

Hydroxyl

Answer 21

-OH

Question 22

Alkoxy

Answer 22

-OR

Question 23

Hemiacetal

Answer 23

OH
         |
     R-C-O-R'
         |
        H

Question 24

Hemiketal

Answer 24

OH
         |
     R-C-O-R'
         |
        R''

Question 25

Mesyl Group

Answer 25

O
         ||
CH3-S-
         ||
         O

Question 26

Tosyl Group

Answer 26

O
         ||
    Ar-S-S
         ||
         O

Question 27

Carbonyl

Answer 27

O
||
-C-

Question 28

Acetyl

Answer 28

O
||
-C-CH3

Question 29

Acyl

Answer 29

O
||
-C-R

Question 30

Anhydride

Answer 30

O O
|| ||
R-C-O-C-R

Question 31

Aryl

Answer 31

-Ar

Question 32

Benzyl

Answer 32

Ar-CH2-

Question 33

Hydrazine

Answer 33

N-N

Question 34

Hydrazone

Answer 34

R=N-N

Question 35

Vinyl

Answer 35

CH2=CH-

Question 36

Allyl

Answer 36

CH2=CH
|
CH2-

Question 37

Vinylic

Answer 37

C=C-X

Question 38

Nitrile

Answer 38

C-3-N

Question 39

Epoxide

Answer 39

O
/ \
C - C

Question 40

Enamine Imine

Answer 40

CR2
||
R-C-NRH

CR2
||
R-C=NR

Question 41

Oxime

Answer 41

R
|
R-C-N-OH

Question 42

Nitro

Answer 42

O
    ||
  -N+
    ||
   O-

Question 43

Nitroso

Answer 43

-N=O

Question 44

Structural Isomers

Answer 44

Same molecular formula, diff bond to bond connection

Question 45

Conformational Isomer and types

Answer 45

Same molecular formula, diff spacial orientation

Anti-staggered (high priority groups very separated)

Question 46

Stereoisomer

Answer 46

Same molecular formula and bonds

Question 47

Enantiomers

Answer 47

Non-Superimposavle mirror images

Question 48

Determining Absolute Configuration

Answer 48

R (clockwise) or S (counterclockwise)

1. Det. high and low priority atoms by atomic wt. (x bonds)
2. Point lowest grp into page
3. Draw circle high to low

Question 49

Relative Configuration

Answer 49

Differ in only 1 substituent around C, other substituents oriented identically

Question 50

Optical Inactivity

Answer 50

Due to racemic mixture

Question 51

Optical Activity

Answer 51

Must be chiral and enantiomers are separated

Question 52

Diastereomers

Answer 52

Same molecular formula, same bonds, NOT mirror images, NOT same compound

Question 53

Epimers

Answer 53

Diastereomers that differ in 1 chiral C

Question 54

Anomers

Answer 54

Cyclic diastereomers formed when ring closes at epimeric C

Question 55

Cis/Trans isomers

Answer 55

Cis: same side, dipolar moment, sterically hindered
Trans: opposite sides, no dipolar moment

Question 56

Cis/Trans w/ tri/tetra substituted alkenes

Answer 56

E=high priority substituents on opposite sides

Z=high priority substituents on same sides