Organic Chem Chapter 9

 

What is NaNH2?

Sodium Amide.

*a base that is normally used to deprotonate terminal alkynes to create acetylide anions
 

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Deprotanation of terminal alkyne
*creates a acetylide ion which is a nucleophile
*reacts with primary alkyl halides only to form new internal alkynes
What is the outcome of an Alkyne reacting with Br2 and what type of reaction is it?

Addition of X2

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What does saturation of a Alkyne with Hydrogen do?

 

Alkyne reduces to alkane with H2 in presence of (Pd/C) or (Pt)

What is this reaction called?

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Hydrogenation 

To reduce alkyne to a Cis alkene you need to use…..

 

 

H2 and a Lindar Catalyst

What is an Enol?

*an OH on a double bonded carbon

*Unstable
-en (alkene) -ol (alcohol) 

Which reaction creates enols which are unstable and rapidly converts into only ketones?

 

 

Oxymercuration/Mercury (II) Catalyzed hydration

What is tautomerization?
Reaction that converts Enol into Ketone

what are tautomers?

Give an example.

Molecules that differ only in placement of a double bond and a hydrogen

 

Example: Enol and Ketone

What is the name of an reaction that is antimarkovnikov, and ends with an aldehyde or Ketone?

What is the reagent used?

*Hydroboration

 

*BH3, THF, & H2O2

To reduce an Alkyne to a Alkane what catalyst must be used with H2?

 

 

Pd/C

 

What agents are needed to reduce a alkyne  to a trans alkene?

Lithium(Li) or Sodium(Na) metal in the presence of Ammonia (NH3)
Oxidative cleavage [KmNO4 or O3]of internal Alkyne will produce..

2 Carboxylic acid products

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Oxidative Cleavage [KmNO4 or O3] of a terminal alkyne will produce…
Carboxylic acid and CO2
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