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CHEM 341 Reactions
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36
Organic Chemistry
Undergraduate 2
12/08/2013

Additional Organic Chemistry Flashcards

 


 

Cards

Term
Alcohol--->Alkyl Halide
Definition

Alcohol+HX

 

-H adds to OH and makes it better leaving group

-Usually SN1 unless SOCl2 or PBr3 are used

-SOCl2 and PBr3 cause inversion (SN2)

Term

Ether-------->alkyl halide

 

Definition

Ether+2HX

 

-ROR' splits to form two separate alkyl halides

Term
Alkene---->Alkyl Halide
Definition

Alkene+HX

 

-Adds according to Markovnikov's Rule unless HBr in presence of peroxides

Term
Alkene---->vic-dihalide
Definition
Alkene+X2 in organic solvent (DCM)
Term
Alkyne---->gem-dihalide
Definition
Akyne+2HX
Term
Alkyne---->Tetrahalide
Definition
Alkyne+2X2
Term
Alkyl halide---->Alcohol
Definition

Alkyl halide+-OH

 

-Regular Substitution

Term
Epoxide---->Alcohol
Definition

Epoxide+Acid (HA)

 

-Acid attacks more substituted side

-H adds to oxygen

 

-OR-

 

Epoxide+1.STRONG Nu:-

2.H2O

 

-Nu adds to less sub side

Term
Alkene---->Alcohol
Definition

Alkene+H2O/H2SO4 (Markovnikov's Rule)

 

-OR-

 

Alkene+1.BH3

                             2.H2O2/OH-(A-MR)

Term
Alkene---->anti-1,2-diol
Definition

Alkene+1.RCO3H

                         2.H2O (OH- or H+)

 

-Epoxidation followed by ring-opening

Term
Alkene---->syn-1,2-diol
Definition

Alkene+KMnO4/H2O, OH-

 

-OR-

 

Alkene+1.OsO4

                       2.NaHSO3, H2O

Term
Alkyl halide---->ether
Definition
Alkyl halide+-OR'
Term
Alkene---->ether
Definition
Alkene+R'OH in H2SO4
Term
Alcohol---->tosylate (ROTs)[+Cl-+pyridinium]
Definition
Alcohol+TsCl in pyridine
Term
Halohydrin---->epoxide
Definition
Halohydrin+base
Term
Alkene---->epoxide
Definition
Alkene+RC(=O)OOH in mCPBA
Term
Alkene---->halohydrin
Definition

Alkene+X2 in presence of H2O

 

-OH attacks more sub side

Term
Alkyl halide---->alkane
Definition

Alkyl halide+1.LiAlH4

                2.H2O

Term
Alkene (or alkyne)---->alkane
Definition

Alkene (or alkyne)+(2)H2 on solid Pd-C

 

-Catalytic addition

Term
Alkyl halide---->alkene
Definition
Alkyl halide+bulky base (with heat)
Term
Alcohol---->alkene
Definition

Alcohol+H2SO4 (or tosic acid)(and heat)

 

-OR-

 

Alcohol+POCl3 (in pyridine)

Term
Tosylate---->alkene
Definition

Tosylate+bulky base (in heat)

 

-E2

Term
Alkyne---->syn-alkene
Definition
Alkyne+H2 (Lindlar's catalyst)
Term
Alkyne---->anti-alkene
Definition

Alkene+ Na (in NH3(l))

 

-Dissolving metal reduction

Term
Dihalide---->alkyne
Definition

Dihalide+2NH2-

 

-OR-

 

tBuO- (in DMSO)

 

-Two separate E2 reactions

Term
Alkyne---->aldehyde
Definition

Terminal alkyne+1.BH3

                                2.H2O2/OH-

 

-Anti Markovnikov's Rule

Term
Alcohol---->Aldehyde
Definition
Primary Alcohol+PCC
Term
Alkyne---->ketone
Definition

INTERNAL Alkyne+1.BH3

                                  2.H2O2/OH-

 

-OR-

 

Alkyne (either)+H2O/H2SO4

Term
Ether---->Alcohol
Definition

Ether+H-X

 

-If R groups are differenct (ROR') will create mixture of 4:

1.RO

2.XR'

3.R'O

4.XR

Term
Alcohol---->Ketone
Definition

Secondary alcohol+any Cr6+ reagent

 

-Cr6+ Reagents:

CrO3/H2SO4

Na2Cr2O7/H2SO4

K2Cr2O7/H2SO4

Term
Alkene---->Aldehydes/Ketones
Definition

Alkene+1.O3

                                   2.Zn/H2O or CH3SCH3

 

-Splits alkene (ozonolysis)

Term
Alkyne---->Carboxylic Acid
Definition

Alkyne+1.O3

             2.H2O

 

-Internal makes two carboxylic acid molecules

-Terminal makes carboxylic acid and CO2

Term
Alcohol---->Carboxylic Acid
Definition

Primary Alcohol+Oxidizing Agent

 

-can also make an aldehyde (PCC in CH2Cl2)

-Oxidized by Na2Cr2O7, CrO3, or K2Cr2O7 in H2O/H2SO4

Term
Alcohol---->Ether
Definition

SN2: 2 Primary alcohols+H2SO4 (and heat)

 

-OR-

 

2 Primary alcohols+H+

 

-OR-

 

Asymmetrical: Alcohol+Strong base+R'-X

Term
Aldehyde---->Carboxylic acid
Definition
Aldehyde+KMnO4 (in MeOH/H2O)
Term
Epoxide---->1,2-diol
Definition
Epoxide+NaOH or H3O+
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