Organic Chemistry

Front 1

ROH+ HX yields

Back 1

RX + H20

(Alkyl Halide from Alcohol and Hydrogen Halide)

Front 2

ROH + SOCl2/PBr3

Back 2

RCl/RBr (for 1*, 2* Alcohols)

Front 3

R3CH + Cl2

Back 3

R3CCl

reagents: Cl2, light

Front 4

ROH + Acid yields

Back 4

Alkene

reagents: acid catalyzed (H2SO4, H3PO4,)

Front 5

RX + Base yields

Back 5

Alkene

reagents: weak base (H3C2O-)

Front 6

Alkene + H2/Pd

Back 6

Alkane

Front 7

Alkene + HX

Back 7

RX (Alkane)

Front 8

Alkene + HBr

Back 8

RX (Alkane)

reagents: ROOR
anti-Markovnikov

Front 9

Alkene + Acid

Back 9

RX

Front 10

Oxymercuration of Alkene

Back 10

Yields Alcohol

Reagents: Hg(OAc)2, H20, NaBH4

Front 11

Hydroboration-Oxidation of Alkene

Back 11

Yields Alcohol

Reagents: BH3, THF
Then H2O2, NaOH, H20

anti-Markovnikov syn addition

Front 12

X2 to Alkene

Back 12

yields vicinal dihalide alkane

anti-Markovnikov anti addition

Front 13

Prepare Vicinal Halohydrin from Alkene

Back 13

yields vicinal halohydrin

reagents: X2, H20

OR NBS, DMSO, H20

X adds anti-Markovnikov anti addition

Front 14

Epoxidation of Alkene

Back 14

yields epoxy

reagents: H3CCO2OH

Front 15

Ozonolysis

Back 15

cleaves alkene bonds with C=O bonds.

Front 16

Alkylation of Acetylene

Back 16

yields longer alkynes

reagents: NaNH2, NH3, ethere

Front 17

Preparation of Alkynes by elimination

Back 17

yields alkynes through doubledehydrogenation + 2HX

reagents: 3 eq. NaNH2, NH3

Front 18

Hydrogenation of Alkynes

Back 18

yields alkanes
reagents: H2, Pd/C

Front 19

Lindlar's Catalyst to Alkynes

Back 19

yields CIS-ALKENE
reagents: H2, Lindlar's

Front 20

Metal Ammonia Reduction of Alkynes

Back 20

yields TRANS-ALKENE
reagents: Na, NH2, HOC(CH3)3

Front 21

HX to Alkynes

Back 21

yields geminal dihaloalkane in excess HX

yields trans-alkene with equal HX

Front 22

HBr to Alkyne

Back 22

yields trans-alkene with Br

reagents: ROOR

anti-Markovnikov

Front 23

Hydration of Alkyne

Back 23

yields enol/keto tautomerization
results in alkyl aldehyde/ketones

reagents: HgSO4, H2SO4, H20

Front 24

X2 to Alkyne

Back 24

yields tetrahaloalkanes in excess X2

yields trans-alkene with equal X2

Front 25

ozonolysis of Alkynes

Back 25

yields carboxylic acids

reagents: O3, Zn

Front 26

Hydroboration oxidation of Alkynes

Back 26

yields aldehydes of ketones

reagents: BH4, THF, NaOH, H20, H202

Front 27

NBS to cyclohexene

Back 27

yields anti-Markovnikov addition of Br

reagents: NBS, light, CCL4

Front 28

which orbitals do diene/dienophile interacts?

which represent e- withdrawing, e-donating?

Back 28

diene: HOMO, e-donating
dienophile: LUMO, e-withdrawing

(good dienophiles are conjugated carbonyls)

Front 29

Huckle's Rules

Back 29

4n+2 pi electrons
planar
conjugated

Front 30

Birch Reduction of Benzene

Back 30

yields nonconjugated diene

reagents: Na(0), NH3, (H3C)3COH

Front 31

Free radical halogenation of alkylbenzene

Back 31

yields substitution at benzylic hydrogen only

reagents: NBS, light, ROOR

Front 32

oxidation of alkylbenzenes

Back 32

results in carboxylic acids (benzoic acid)

reagents: KMnO4 or Na2Cr2O7, H2SO4

cleaves everything past benzylic carbon, replaces with COOH

Front 33

aromatic ions

Back 33

cyclopropenyl cation
cyclopentadienyl anion
cycloheptatrienyl cation

Front 34

nitration of benzene

Back 34

reagents: HNO3, H2SO4, H20

Front 35

sulfonation of benzene

Back 35

SO3, H2SO4, H20

Front 36

halogenation of benzene

Back 36

X2, FeX3

Front 37

Friedel-Crafts Alkylation

Back 37

removes chloride from alkane, attaches onto benzyl

AlCl3

*rearrangement possible)

Front 38

Friedel-Crafts Acylation

Back 38

removes chloride from carbonyl, attaches onto benzyl

AlCl3

Front 39

Synthesis of Alkyl benzenes

Back 39

First, undergo Friedel-Crafts acylation
Then, reduce carbonyl (removes C=O) through

Zn(Hg), HCl
or
H2NNH2, KOH

Yields Alkylbenzene

Front 40

patterns for electrophilic substitution

Back 40

e- donating - activating - ortho,para director

e-withdrawing - deactivating - meta director (exception halides)

meta-directors: any CARBONYL attached to benzene,

_
C=N
CF3
NO2

Front 41

preparation of organometallic compound

Back 41

alkyl halide with 2 metal eq.

RCH3Cl + 2M yielids RCH3M

Front 42

synthesis of alcohols using grignard

Back 42

grignard reagents react with aldehydes, ketones, esters to afford alcohols

aldehydes afford 2*
ketones afford 3*
esters afford 3*

reagents:
MgBr, ether/THF

Front 43

synthesis of acetylenic alcohols

Back 43

rxn. first btwn terminal acetylene and RMgBr to yield acetylide anion

acetylide anion reacts with carbonyl to form alcohol

reagents:MgBr, ether/THF, H20

Front 44

alkane synthesis through organo copper reagents

Back 44

alkyl lithium reacts with copper halide to produce lithium dialkyl cuprate, which reacts with alkyl halid to produce alkanes by C-C bond formation

R2CuLi + R'X yields RR'

reagents: ether

Front 45

cyclopropane formation

Back 45

addition of carbon ring to alkene

using carbenes -
reagents CHCl3, KOH (yeilds dicholorocyclo)

using organozinc
reagents ZnCu, CH2I2, ether

Front 46

synthesis of alcohols by reduction of aldehydes and ketones

Back 46

adding metal hydride (H:-)

reduces aldehydes to 1* alcohols
reduces ketones to 2* alcohols

reagents: NaBH4, LiAlH4
ether
then H30+

Front 47

synthesis of alcohols by reduction of esters and carboxylic acids

Back 47

reduces to 1* alcohols

reagents: ONLY LiAlH4
ether
then H30+

Front 48

synthesis of alcohols from epoxides

Back 48

reduces to 1* alcohol

reagents: R-MgBr+

yields: HO-CH2-CH2-R

Front 49

synthesis of diols

Back 49

results in vicinal, syn addition

reagents: OSO4, (CH3)3COOH, tBtOH

Front 50

synthesis of ethers BY alcohols

Back 50

alcohols

reagents: H2SO4

Front 51

synthesis of esters

Back 51

add alcohols with carboxylic acid

ROH + R'COOH -> RCOOR'

reagents: HA, H2SO4

can also be formed via rxn. of acyl chloride or acid anhydride w/ an alcohol

RCOCl + HOR' -> RCOO'R'

reagents: pyridine

Front 52

esters of inorganic acids

Back 52

nitric acid + alcohol

sulfuric acid + alcohol

Front 53

oxidation of alcohols

Back 53

2* alcohols oxidized to ketones
1* alcohols usually oxidized to carboxylic acids

reagents: KMnO4/Na2Cr2O7, H2SO4

1* alcohol can oxidize to aldehyde w/t PCC or PDC reagents

Front 54

oxidative cleavage of vicinal alcohols

Back 54

two R2COH bonds cleave as well as C-C bond btwn and form C=0 bonds.

reagents: NaIO4/HIO4

Front 55

thiols

Back 55

RSH + R'X yield RSR'

reagents: NaF, THF