Carboxylic Acids Flashcards
what is the end name of carboxyic acids [COOH]?
—oic acid
what are COOH salts named ?
—oate
what are dicarboxylic acids named?
—dioic acids
Why do carboxylic acids have high boiling point?
H bonding
how do COOH exist?
they exist as dimers
What makes a carboxylic acid’s acidity enhanced?
resonance bet O atoms
electron withdrawing substituents
mneumonic for numbering priorities
C E Am N Al Am Al Al Et H (ceam nalal eth)
COOH | COOR | CON | C=N triple bond | COH | C=O | CNh2 | C=C | C triple C | O grp | X
explain the O2 resonance on carboxylic acid
C is +ve, O is -ve with [no = bond]
O of OH is +ve, O is -ve, [=bond bet C&O of OH]
What is the melting, boiling point, and solubility of carboxylic acid compared to alcohols?
all are higher than alcohols
what is alpha C?
C attached to the C of COOH
name some electron withdrawing substituents
Nitro group (-NO2)
Cyano group (-CN)
Carbonyl groups (-C=O) like aldehydes and ketones
Halogens (-F, -Cl, -Br, -I)
Trifluoromethyl group (-CF3)
What can increase the acidity of benzoic acid?
Electron withdrawing groups on C-2
carboxylate ion
COO-
micells
C chains of 12-18 Cs will form circles
what are the 4 reactions to form COOH acid?
1° OH
aldehyde
methyl benzene
alkyne
all of these can react with oxi agents (such as H2Cr2O7, KMnO4, O3) to form COOH
lactam
cyclic amide
lactone
cyclic ester
anhydride
O=C-O-C=O
how is soap formed ? the process of saponification ?
mixing
long chain COOH (fatty acids) + strong base = soap
amide
O=C-NH
Ester
COOH + OH = ester (O=C-OR)
reactivities in Sn rxns of COOH derivaties
anhydrides > ester >amides
induction
Uneven distribution of charge across a sigma bond because of difference in electronegativity
conjugation
3 or more atoms with ability to resonate are near each other
a highway to connect electrons from 1 side to another
wwhich amines can react with estersto form amides ?
1° and 2° only
proton
H+
How are the products of a reduction reaction different than their reactants?
There are more C-H bonds in the products than the reactants of reduction reactions
hydrogen atom
H. (H with proton)
hydride ion
H..- (H with 1 protons and 2 electron)
name reducing agents
NaBH4
LiAlH4
decarboxylation
Loss of CO2 from a molecule
alkyl group
C-H group
hydroxy group
O-H group
oxo group
C=O group
why carboxylic acids cannot undergo substitution reactions at the a-carbon?
because a base removes a proton from the OH group instead of from the a-carbon, since the OH group is more acidic