Organic Chemistry

Front 1

Substitutive Method for naming Alcohols

Back 1

base=longest chain w/ OH
OH gets lowest possible #
name ends in "ol" ("anol")
precede name w/ OH locant # (unless number is 1)

DOES NOT INCLUDE HYDROXY

Front 2

Molecularity

Back 2

# of species involved in a chemical reaction on the reactant side

Front 3

Major Reaction Types

Back 3

Substitution
Elimination
Addition
Rearrangement

Front 4

Polycyclic (Bridged/Fused) Nomenclature

Back 4

# rings = # bond cleavages that must be broken to open ring to non-cyclic (bicyclic, tricyclic...)
1. base name is by total #carbons
2. bracket the numbers of the carbons connecting the bridge heads (don't count bridge heads) from high to low
3. ___cyclo[#.#.#]basename

Front 5

Polycyclic (Spiro) Nomenclature

Back 5

1. base name is total #carbons
2. bracket (lowest to highest) the number of carbons connecting spiro carbon along each pathway (don't count spiro carbon)
3. spiro[#.#]basename

Front 6

Base name when rings and chains are present in the same molecule

Back 6

base is largest component
(if same size, either is acceptable)

Front 7

Complex Alkyl Nomenclature

Back 7

name as normal with locant numbers, end in -yl and place in ( )

Front 8

-CN

Back 8

cyano

Front 9

-NH2

Back 9

amino

Front 10

-NO2

Back 10

nitro

Front 11

isomers

Back 11

conformational - isomers that can be interconverted by bond rotations
stereo - differ in spatial arrangement, CANNOT be interconverted by bond rotations
constitutional - differ in bonding patters of atoms

Front 12

C=O

Back 12

carbonyl

Front 13

Bases for Dehydrohalogenation

Back 13

weak--E1
strong--E2

Front 14

Cahn-Ingold-Prelog Priority System

Back 14

determines priority and relationships for substituents by atomic number (higher number, higher priority)
cis - Z
trans - E

Front 15

vinyl

Back 15

-CH=CH2

Front 16

allyl

Back 16

-CH2CH=CH2

Front 17

isopropenyl

Back 17

CH3
|
-C=CH2

Front 18

Ar-alkyl in NMR

Back 18

slightly broadened singlet
5 hydrogen integration

Front 19

X-Ar-X

Back 19

equivalent H singlet
4 hydrogen integration

Front 20

X-Ar-Y

Back 20

two sets of two '||'
4 hydrogen integration

Front 21

Z
|
Ar-C=O

Back 21

two complex multiplets
2:3 hydrogen integration
2 @ higher ppm

Front 22

Strong Bases

Back 22

metal alkoxides
RO(n)M(p) + HA -> ROH + MA

Front 23

Weak Bases

Back 23

alcohols
ROH + MA -> RO(p)H2 + A(n)

Front 24

Rearrangements

Back 24

hydride shifts
methyl shifts
ring contractions
ring expansions

Front 25

Alkynes in IR

Back 25

if symmetric, triple bond will not show up on the IR spectrum

Front 26

Equivalent hydrogens in NMR

Back 26

do not split each other, even if on adjacent carbons

Front 27

Synthesis of alkenes

Back 27

Elimination
Dehydration
Dehydrohalogenation

Front 28

Zaitsev's Rule

Back 28

when multiple alkene products are formed, major is the most alkyl substituted

Front 29

Determining Major Products

Back 29

1. more stable carbocation
2. Zaitsev's Rule
3. largest groups trans (E)

Front 30

Hydrogenation of Alkenes

Back 30

H2
----->
M (M=Pt,Pd,Ni)

Adds H and H
syn addition to least sterically hindered face

Front 31

Hydrohalogenation of Alkenes

Back 31

HX (X=Cl,Br,I)
---->

Adds H and X
Markovnikov
syn/anti random

Front 32

Hydration of Alkenes

Back 32

H2SO4
------->
H2O

Adds H and OH
Markovnikov
syn/anti random

Front 33

Free Radical Addition of HBR to Alkenes

Back 33

HBR
------>
ROOR/hv

Adds H and Br
Anti-Markovnikov
no rearrangements

Front 34

Hydroboration-Oxidation of Alkenes

Back 34

1.)B2H6
------------>
2.)H2O2/NaOH

Adds H and OH
Anti-Markovnikov
syn addition

Front 35

Halogenation (X and X) of Alkenes

Back 35

X2 (X=Cl,Br)
---->

Adds X and X
anti addition
no rearrangements

Front 36

Halogenation (X and OH) of Alkenes

Back 36

X2 (X=Cl,Br)
----->
H2O

Adds X and OH
anti addition,OH on more stable
no rearrangements

Front 37

Epoxidation of Alkenes

Back 37

RCO3H
------->
o
Adds /_\
syn addition
no rearrangements

Front 38

Ozonolysis of Alkenes

Back 38

1.)O3
------->
2.)H2O,H2O/Zn,Me2S

breaks bonds
converts to carbonyls
aldehyde products use Me2S or H2O/Zn to keep as aldehydes
use H2O to convert aldehyde to carboxylic acid

Front 39

Dehydration to synthesize Alkenes

Back 39

H2SO4,H3PO4,KHSO4
------------------>

uses acids

Front 40

Dehydrohalogenation to synthesize Alkenes

Back 40

H2O
----->

uses bases

Front 41

Radical Halogenation of Alkanes

Back 41

X2 (X=Br,Cl)
------->
heat/light

RH----->RX
involves radicals

Front 42

Reaction of Alcohols with HX for Alkanes

Back 42

HX (X=Br,Cl)
----->

ROH----->RX
involves carbocations

Front 43

Alkylation of Terminal Alkynes

Back 43

1.)NaNH2,LiR
---------------->
2.)alkyl halide

Adds alkyl group
NaNH2 makes Ammonia biproduct
needs strong base
Sn2 mechanism
limited to methyl/primary alkyl halides

Front 44

Hydrogenation of Alkynes

Back 44

H2
----> alkanes
Ni

H2
----------> alkenes
Lindlar Pd

Adds H and H
syn addition

Front 45

Metal Ammonia Reduction of Alkynes

Back 45

M (M=Li,Na,K)
----->
NH3(l)

Reduces to trans alkenes
combines ionics and radicals
no rearrangements

Front 46

Markovnikov Hydrohalogenation of Alkynes

Back 46

1eq HX
-------> alkenes

Add H and X
anti addition

2eq HX
-------> alkanes

sequential, geminal products
no rearrangements

Front 47

Anti-Markovnikov Hydrohalogenation of Alkynes

Back 47

1eq HX
---------> alkenes
ROOR/light

Adds H and X

2eq HX
---------> alkanes
ROOR/light

Adds 2H and 2X
vicinal products
no rearrangements

Front 48

Hydration of Alkynes

Back 48

H2SO4
--------->
H2O/HgSO4

keytone products
Markovnikov
no rearrangements

Front 49

Hydroboration Oxidation of Alkynes

Back 49

1.)BH3
----------->
2.)H2O/NaOH

Anti-Markovnikov
terminal alkynes=aldehydes
internal alkynes=keytones
no rearrangements

Front 50

Halogenation of Alkynes

Back 50

X2 (X=Cl,Br)
------>

Adds X and X
anti addition
transhalide products
no rearrangements

Front 51

Ozonolysis of Alkynes

Back 51

1.)O3
------->
2.)H2O

carboxylic acid products
no rearrangements

Front 52

Allylic Halogenation

Back 52

X2 (X=Cl,Br)
------->
NXS (NCS,NBS)

NCS/NBS used so dihalides don't form

Front 53

Benzylic Halogenation

Back 53

X2 (X=Cl,Br)
---------->
NCS,NBS/hv

Adds X to benzylic carbocation

Front 54

Benzylic Sn1 Reactions

Back 54

EtOH
------>
/\

easier and faster than allylic Sn1 reactions

Front 55

Benzylic Elimination Reactions

Back 55

NaOMe
------->
MeOH

most stable double bond is conjugated with ring, if possible

Front 56

Benzylic Electrophilic Addition

Back 56

HBr
----->

Adds Br to benzylic carbon

HBr
------>
ROOR

Adds H to benzylic carbon

Front 57

Oxidation of Alkyl Side Chains

Back 57

Na2Cr2O7 or KMnO4
--------> ------>

turns any alkyl group with at least one benzylic hydrogen to carboxylic acid functional group

Front 58

Electrophilic Aromatic Substitution

Back 58

1.) E
------->
2.)base

electrophile substitutes for one ring hydrogen

Front 59

Nitration of Benzene

Back 59

H2SO4
------->
HNO3

substitutes ring hydrogen with NO2

Front 60

Sulfonation of Benzene

Back 60

H2SO4
------->

substitutes ring hydrogen with SO3H

Front 61

Halogenation of Benzene

Back 61

X2 (X=Cl,Br)
-------->
AlCl3,FeBr3

substitutes ring hydrogen with X

Front 62

Friedal Crafts Alkylation

Back 62

adds alkyl group

RX
--------->
AlCl3,FeBr3,ZnCl3

ROH
-------->
BF3

alkene
--------->
H2SO4

Front 63

Friedal Crafts Acylation

Back 63

keytone products

Cl
|
R-C=O
-------->
AlCl3

no rearrangements

Front 64

Clemmensen Reduction

Back 64

Zn(Hg)
-------->
HCl

removes =0 after F.C. acylation

Front 65

Wolff-Kishner Reduction

Back 65

H2NNH2
--------->
KOH/heat

removes =O after F.C. acylation

Front 66

Activating o/p directors

Back 66

-NH2 -NHR -NR2 -OH
-OR -R -Ar -C=C

R R R
| | |
-N-C=O -N-C=O -O-C=O
| |
H R

Front 67

Deactivating Meta Directors

Back 67

-NO2 -CF3 -SO3H

Y
|
-C=O -C(triplebond)N

Front 68

Deactivating o/p directors

Back 68

-X -CH2X

Front 69

Ring Formation via F.C. Reactions

Back 69

intramolecular

AlCl3
------->
high
dilution