Exam 2 - Oxidation/Reduction Flashcards
Three important functional groups in oxidation:
aldehyde, ketone, carboxylic acid
When reacting aldehydes/ketones with Grignards/Organolithiums, the ___ ___ attached to the Metal simply adds on the central C, eliminating the C=O double bond. H3O+ then converts the O- to ___.
R group (alkyl group), OH
Oxidation = ___ hydrogens, not Cs.
removing
A ___ alcohol can be oxidized to a ketone.
secondary alcohol
Examples of Weaker Nucleophiles:
H2O, ROH
An aldehyde reacting with a Grignard/Organolithium reagent and a follow-up H3O+ step, will produce a ___ ___.
secondary alcohol
Oxidation - The substitution of ___ bonds for ___ bonds.
C-H bonds for C-X bonds
Simplest aldehyde: ___
formaldehyde
___ - The substitution of C-H bonds for C-X bonds (X = O,F,Cl,Br,I,N, etc.)
Oxidation
___ ___ -> Acid-catalyzed and reversible.
Weaker Nucleophiles
*Reminder: Grignard and Organolithium reagents CANNOT work around ___ ___ (i.e. ___). They need a separate ___ ___ step.
acidic protons (i.e. OH), separate acidic workup step (H3O+)
In Pinnick Oxidation, an aldehyde reacts with the oxidants: NaClO2, NaH2PO4 to become a ___ ___.
carboxylic acid
A secondary alcohol can become a ketone via the oxidants:
DMP, PCC, Swern oxidation (DMSO, NET3), and Jones Reagent (CrO3, H2SO4)
You can cleave a ___ ___ with NaIO4!
vicinal diol
A ketone reacting with a Grignard/Organolithium reagent and a follow-up H3O+ step, will produce a ___ ___.
tertiary alcohol
Simplest organic molecule: ___
CH4 (methane)
A ___ alcohol reacting with Jones Reagent (CrO3, H2SO4) will become a carboxylic acid.
primary alcohol
A primary alcohol reacting with ___ ___ will become a carboxylic acid.
Jones Reagent (CrO3, H2SO4)
A secondary alcohol can be oxidized to a ___.
ketone
You can cleave a vicinal diol with ___!
NaIO4
Examples of STRONG Nucleophiles:
RMgBr, RLi, OH-, CN-, LiAlH4, NaBH4
A primary alcohol can become an aldehyde via the oxidants:
DMP, PCC, or Swern oxidation (DMSO, NEt3)
Hydride-Reducing Agents such as ___ or ___ can convert aldehydes to primary alcohols, or ketones to secondary alcohols.
NaBH4, LiAlH4
In ___ ___, an aldehyde reacts with NaClO2 and NaH2PHO4 to become a carboxylic acid.
Pinnick Oxidation
Hydride-Reducing Agents such as NaBH4 or LiAlH4 can convert aldehydes to ___ ___, or ketones to ___ ___.
primary alcohols, secondary alcohols
___ = Removing hydrogens, not Cs.
Oxidation
When using Hydride-Reducing Agents, remember that they need a separate ___ ___ step.
separate acidic workup step (H3O+)
Strong Nucleophiles -> ___ or ___.
Basic or Neutral
Weaker Nucleophiles -> ___ and ___.
Acid-catalyzed and reversible
A primary alcohol can be oxidized to a(n) ___.
aldehyde
Oxidation = Removing ___, not Cs.
hydrogens
Hydride-Reducing Agents such as NaBH4 or LiAlH4 can convert ___ to primary alcohols, or ___ to secondary alcohols.
aldehydes, ketones
In Pinnick Oxidation, an aldehyde reacts with the oxidants: ___ and ___ to become carboxylic acid.
NaClO2, NaH2PO4
Tertiary carbons are usually ___ to oxidatoin.
unreactive
___ carbons are usually unreactive to oxidation.
tertiary
A formaldehyde reacting with a Grignard/Organolithium reagent and a follow-up H3O+ step, will produce a ___ ___.
primary alcohol
Aldehydes and ketones can also be reduced by catalytic reduction with ___ and ___. The problem here though, is that other functional groups such as ___ can get reduced first.
H2 and Pt/Ni, alkenes
A ___ alcohol can be oxidized to an aldehyde.
primary alcohol
In Pinnick Oxidation, a(n) ___ reacts with the oxidants: NaClO2 and NaH2PO4 to become a carboxylic acid.
aldehyde
A primary alcohol reacting with Jones Reagent (CrO3, H2SO4) will become a ___ ___.
carboxylic acid
You can ___ a vicinal diol with NaIO4!
cleave
___ ___ -> Basic or Neutral.
Strong Nucleophile
