Chapter 21 Flashcards
Carboxylic acid derivative
RC=OX
X=-OR
Ester
X=-NR2
Amide
X=-X
Acid halide
X=-COOR
Anhydride
“Mono” acids
Take off E, add “oic acid”
Mono acid with ring
Name it as ring, add carboxylic acid
Formic acid r group
H
Acetic acid r group
CH3
Propionic acid r group
CH3CH2
Butyric acid r group
CH3CH2CH2
Benzoic acid R group
Phenol
Diacids(with 2 carbocylic acid groups)
Use “dioic acid” as suffic
Are carboxylic acids or similar alcohols more acidic? Why?
Carbox acids, conjugate bases are more stable
What effect do electron withdrawing groups have?
Make conjugate bases more stable, make compounds more acidic
Closer electron withdrawing groups
Increase acidity
- R triple bonded to R with 1. O3 2. H2O
2 RCOOH
RCH3OH with Na2Cr2O7, H2SO4
RCOOH
Phenol bound to isopropyl,Na2Cr2O7, H2SO4
Phenol bound to COOH
R-C triple bound to N reacted with H3O+ and heat
RCOOH
RMgBr reacted with CO2 and H3O+
RCOOH
Reduction of acid yields an
Alcohol (LAH OR 1. BH3, THF 2. H2O2, NaOH can be used)
To name an acid halide
Replace ic acid with yl halide
Acid halide bound to ring
Carbonyl Xide
Acid anhydride
Anhydride
Esters
Ate
Amide
amide
Amide bound to ring
Carboxamide
Nitrile
Onitrile
Least to most reactive
OH, NR2, OR, OCOR, Cl
The more stable the leaving group
The more reactive the compound is
If a reaction takes place in an acid
Don’t form basic stuff
If a reaction takes place in a base
Don’t form acidic stuff
What always happens?
NA, LLG
Is it easier to make things more or less reactive?
Less
What can make things more reactive?
SOCl2/COCl2 (replaces with Cl)
Acid halide with 1. LAH 2. H2O
RCH2OH
Acid halide with 1. LiA(o t butyl)3H
2. H2O
Aldehyde (H)
- XS RMgBr
Replaces Everything with R
- R2CuLi
- H2O
Changes acid halide to ketone
Reactions with (RC(O))2)O-
1. 2 MECOOH with heat
Fuses them, water as byproduct
RCOCl with RCOO
Anhydride plus salt
Is (RC(O))2)O nucleophiles or electrophiles?
Electrophiles
RCOOR with 1. NaOH 2. MeI
Changes H to methyl group
HXO2 with ROH, py
RCOOR, pyr HCl
RCOOR with 1. NaOH 2. H3O+
RCOOH, ROH
RCOOR plus H3O+
RCOOH + MeOH
RCOOR plus NH3 and Heat
Amide
NC=O plus strong reducing agent
Alcohol
NC=O plus weak red agent
Aldehyde
RCOOR plus grignard
Trisub alcohol
Acid plus 1. 2 RLI 2. H3O+
Ketone
HXO2 plus 2 NH3
Amide
2CO joined by O plus 2RNH2
Amide
RCOOR plus RNH2 and heat
Amide
NC=O plus H3O+
Acid (RCOOH
NC=O plus 1. LAH 2. H2O
Amine
RCH2Br plus NACN
Switches Br with Cn
How do you turn an NC=O to a RCN
SOCl2
RCN plus acid
Amide
NC=O plus acid
Acid
RCN plus 1. NaOH, H2O 2. H3O+
Acid
RCN and grignard
Keton
RCN plus 1. XS LAH 2. H2O
Amine