Exam 2 Flashcards
Aldehyde
R’ is H
Carboxylic acid
R’ is OH
Amide
R’ is amine (N with something)
Ketone
R’ is R’
Ester
R’ is OR’
Oxidation
Gaining bonds to O or another EN group
Reduction
Losing bonds to O or another EN group
LiAlH4 (LAH)
Strong reducer, reduces everything to 1° alcohols
NaBH4
Weak reducer, reduces ketones and aldehydes only to 1° alcohols
DIBAL-H
A reducing agent for esters and nitriles that will create an aldehyde
LiAlH(OtBu)3
A reducing agent for acid chlorides that will create an aldehyde
K2CrO4, H3O+
Strong oxidizer, uses -OR substitution with -OH as an intermediate
KMnO4, NaOH
Strong oxidizer, MnO4- and deprotonated alcohol gives the intermediate
Strong oxidizers
Take aldehydes to carboxylic acids
Weak oxidizers
1° alcohols to aldehydes or 2° alcohols to ketones
PCC (Cl-CrO3-)
Weak oxidizer, Cl-CrO3- attaches to alcohol O as LG
Swern oxidation
- OS(CH3)2, (COCl)2
- NEt3
Weak oxidation, reactions stop at the aldehyde and don’t go to carboxylic acid
DMP
Weak oxidation, reaction stops at the aldehyde
Baeyer-Villiger Oxidation
mCPBA, creates an ester and a carboxylic acid
Thioacetals
Reaction of aldehydes/ketones with thiols/thioacetals
Thiols
Contains S (like EtSH, or HS–SH)
Raney Ni, H
Used in ‘desulfurization’ after thioacetal formation to form a carbonyl/CH2
Primary amines + ketone/aldehyde, acid
Formation of imines
Secondary amines + ketone/aldehyde, acid cat
Formation of enamines
HCN
Weak/slow formation of cyanohydrin with ketone/aldehyde
NaCN, KCN
Strong formation of cyanohydrin with ketone/aldehyde
Et2O, R-X and Mg/Li
Formation of organometallics, Mg will form RMgX (Grignard reagent) and Li forms LiX and RLi
Grignard reagents + epoxides
Formation of 2° alcohols with aldehydes and 3° alcohols with ketones
TBSCl, ImH, DmF and then TBAF
TBSCL protects -OH groups so Grignard reagents can add, then removed by TBAF to leave the OH
Phosphorus ylide and aldehyde/ketone
Wittig reaction - forms an alkene (Z isomer only)
Phosphonate ester and aldehyde/ketone
HWE reaction - forms an alkene (E isomer only)
E isomer
Entgegen form - higher atomic priority on opposite sides of a double bond
Z isomer
Zusammen form - higher atomic priority on the same side of a double bond