Orgo 320

Reduction of aldehydes produce this.
Primary Alcohols
Ketones are reduces to give this
Secondary alcohols
Esters are reduced to give
Primary alcohols
Carboxylic acids are reduced to give
primary alcohols
To reduce aldehydes and ketones but not carboxylic acids or esters I would use what reagent?
NaBH4
To reduce aldehydes, and ketones, as well as esters and carboxylic acids I would use what reagent?
LiAlH4
LiAlH4 will add how many H’s to esters and carboxylic acids?
2
Grignard Reactions are especially reactive with what?
Water and Alcohols
Grignard reactions with formaldehyde(CH20) yields what?
primary alcohols
Grignard reactions with aldehydes yield what?
secondary alcohols
Grignard reactions with ketones yield what?
Tertiary alcohols

Esters react with Grignard reagents to yield what?

(Be specific about where the substituents came from)

Tertiary alcohols in which two of the substituents bonded to the hydroxyl bearing carbon have come from the Grignard reagent.;
Dehydrations mean what?
That water is eliminated.;
Dehydration produces?
alkenes
To dehydrate secondary and tertiary alcohols use?
A strong acid like H2SO4
Oxidation of alcohols yields what?
carbonyls
An oxidation reaction that ends in an aldehyde or a carboxylic acid had to come from what kind of alcohol?
Primary
Oxidation of secondary alcohols yields what?
ketones
Oxidation of a tertiary alcohol yields what?
NO RXN
What reagent would we use to prepare an ONLY an aldehyde fron and alcohol, and what type of alcohol would we be using?
Aldehydes come from primary alcohols and if we wanted to isolate the aldehyde we would use PCC.
What reagent would we use for preparing a carboxylic acid from an alcohol and what type of alcohol would we be using?
Primary alcohol and the reagent would be CrO3 or Na2Cr2O7
What reagents would we use to prepare a ketone from an alcohol using oxidation and what type of alcohol would we have started with?
Secondary alcohols are oxidized to yield ketones and we would use CrO3 or Na2Cr2O7
Aryl
Aromatic substituent
These are ALWAYS unreactive in Sn1 and Sn2
Vinylic and arylic
If there are 9H singlets what does that tell me about the structure of the molecule?
Tert butyl is present
Williamson did what reaction?
Ether synthesis
What is a thiol?
SH
What is an epoxide?
Ether in a 3 membered ring
Vinylic
On the double bond
allylic
position next to the double bond
Z rule
Yield the more highly substituted alkene as major.
1700 IR
Carbonyl
UV active means what?
conjugated
What is unique about identical neighboring atoms in NMR.
They don’t split. Twins don’t date.
If something is more conjugated what does that mean about the UV?
It’s higher
6H doublet and 1 multiplet
Isopropyl
2900-3300 IR
C-H
3000-4000 IR
O-H
What does addition of H-X do to an alkene?
It breaks the double bond and adds the X
What does addition of X2 do to an alkene?
It breaks the double bond and adds anti X’s
What type of alcohols work best with HX reactions?
Tertiary
1640-1680
C=C
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