Alcohols And phenols Flashcards
(37 cards)
Describe alcohol nomenclature
1) find longest parents with the OH substituents at the lowest number
2) OH takes highest priority so name the parent chain “alkan-#-ol”
3)if there is more than 1 it is named as “alkanediol or alkanetriol “ ect
Ether nomenclature (R-O-R)
1) no priority against anything
2) acts purely as a substitutent
3) drop “yl “ add oxy
What is a phenol?
A benzene ring with an OH group
Which is more acidic, OH or a phenol and why
Phenol has resonance
What is a grinyard?
R-MG-X group
What yields no reaction when reacted with a grinyard ?
R-X
Aldehyde
R-(c=O)-H
Ketone
R-(c=O)-R
Carboxcylic Acid
R-(c=O)-OH
When does Jones, and SWERN or PPC yield no reaction?
3 degree OH
Describe Jones reaction and reagents
The reagents are Cr2O7(-2) + Acid or CrO3 + acid
1 degree alcohol:
The two h’s on the parent carbon disappear and a double bond to an oxygen takes its place. Basically, we stop once a carboxylic acid is formed
2 degrees OH:
Stop at a ketone
Describe PCC AND SWERN
these reagents are less reactive so always stop at aldehyde
How can we prepare a RO( - ) group from a ROH group? Hint: 2 methods
1) deprotenate with a strong base but NEVER NAOH unless it’s a phenol
2) deprotenate with elemental metal in the form 2k or 2Na
Describe the two ways to prepare ROH from an alkyl halide and list any restrictions or rearrangements
1) SN2 with OH as a nu
-great for any 1 degree Halides, including allylic and benzyllic positions
-NEVER ON 2 (produces alkene) or 3 (NR) degree halides
2) SN1 with water as the nu
-rearrangements are possible
-great for 3 degree or 2 degree halides
How do you prepare ROH from alkenes? 3 options
1) use Hydroboration Oxidation for antimarkovnikov
2) Use Oxymercuration demurcuration for MARK OR H3O+ (for rearrangement if necessary)
3) Use oxidation for the addition of 2 SYN alcohol groups
Hydroboration reagents and type
1) BH3, THF
2) H2O2, NaOH
Anti mark
Oxymercuration demurcuration reagents and type
1) Hg(OAC)2, H2O
2) NaBH4
Markovnikov
Oxidation reagents
KMnO4
OR
OsO4
How do we turn a ketone or aldehyde to an alcohol?
We use a Nu and an Acid Work up. Use a nu to open up the pi bond then react react the O with the strong acid to potentate it.
The nu can be
- RC (triple bond) C(-)
- RMgX
- LiAlH4
How do you prepare organometallics?
React a R-X group with elemental metal
What preparation of organometallics results when we react a halide with elemental Mg?
The magnesium wedges itself in between the R group and the Br and the carbon acts as the Nu
What happens when an R-X group reacts with elemental Li
The X group leaves and is replaced by lithium and the carbon now acts as a NU
What happens when we react grignyards with H20 or OH? Even D2O
The grinyard leaves and is replaced with a H or a D depending on which reagent was used
What happens when you react an organolithium with a 1) ketone in THF and 2) an acid work up?
The pi bond of the oxygen breaks open and has O- on one side and the R group of the organolithium on the other line. Then the acid work up pronates the O to form an oxygen