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Reagents 2
Reagents for Exam 2
34
Chemistry
Undergraduate 3
07/08/2015

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Cards

Term

2 Li

THF or Et2O

Definition
Removes halogen and replaces it with a lithium
Term

1) CH3MgBr

2) NH4Cl (aqueous)

Definition
Reduces aldehyde/ketone to alcohol
Term

1) B2H6 (or BH3 and THF)

2) NaOH, H2O2, H2O

 

Definition

Breaks alkene and adds alcohol to where alkene was

(Hydroboration/Oxidation)

Term

H2

Metal Catalyst (Pd, Pt, Ni)

Definition

Reduces carbonyl to alcohol

Reduces alkenes to alkanes

Term

[(Ph3)P]RhCl

H2

Definition

Wilkinson Catalyst

Reduces least sterically hindered alkene

Term

1) NaBH4

     CH3OH

2) HCl

Definition

Selectively reduces Aldehydes and Ketones

Does NOT reduces esters or carboxyllic acids

Term

LiAlH4, THF, heat

H2O

 

Definition
Reduces aldehydes, ketones, esters, and carboxylic acids
Term

KMnO4

or

OsO4

Definition
Breaks alkene forming a diol
Term

KMnO4

H2O, NaOH

Definition
Breaks alkene (can break open ring structure) creating carboxyllic acids
Term
HIO4
Definition
Breaks ring turning diol into di-aldehyde
Term
KOH (OH-)
Definition

Deprotonates thiol creating negatively charged sulfur ion

Hydrates aldehydes and ketones creating diol

Term
SH (HSK)
Definition
Substitutes thiol in place of halogen
Term

HNO3

H2SO4

Definition
Adds nitro group
Term

Na2Cr2O7

or

K2Cr2O7

 

in H2SO4

Definition

Oxidizes primary alcohol to carboxyllic acid

Oxidizes secondary alcohol to ketone

Does not react with tertiary alcohol

Term

PCC

or

PDC

 

Definition

Oxidizes primary alcohol to form an aldehyde

Oxidizes secondary alcohol to form a ketone

Does not react with tertiary alcohol

Term

DMSO, Oxalyl Chloride

Et2N or Et3N

(Swern Reagents)

Definition

Oxidizes primary alchol to make an aldehyde

Oxidizes secondary alcohol to make a ketone

Does NOT react with tertiary alcohol

Term
O2 (air)
Definition

Adds peroxide (OOH) to ethers

 

Term

H2SO4

Heat

Definition
Creates ether out of two primary alcohols
Term

Ketone

H2SO4

Definition

Turns primary alcohol into ether

Acid protonates the ketone creating a carbocation that is attacked by the oxygen of the alcohol

Term

I2

CH3OH

Definition

I2 Breaks double bond creating the atom ring structure

Alcohol breaks one bond adding to carbon trans to the Iodine

Term
HI
Definition
Breaks ether to form alcohol and alkyl halide
Term
HBr
Definition
Breaks cyclic ether creating hydrocarbon chain with terminal alcohol and halogen
Term
NaS-R
Definition
Sulfur breaks epoxide ring and adds to the least substituted carbon that was part of epoxide ring
Term

CH3MgBr

HCl

Definition

Breaks epoxide ring creating alcohol and methyl group

 

Term

O3

DMS

Definition
Breaks alkene creating two aldehydes
Term

O3

Zn/H2O

Definition
Breaks alkene creating two ketones
Term
HIO4
Definition
Reduces diol to aldehyde
Term

H2SO4

 

Definition
Reduces alkyne to ketone
Term

NaCN, H2O

H2SO4

Definition
Hydrates aldehydes and ketones creating cyanohydrin
Term

HCl

Alcohol

Definition
Creates hemi-acetal then acetal
Term

CH3NH2

H3O, HCl (or BF3 Et2O)

Definition
Creates Imine from ketones and aldehydes
Term

R2NH

Catalytic H2SO4

Definition

Turns aldehyde into enamine

 

Term
Ph3P=R
Definition
Turns ketone into alkene
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