Chapter 19: Carboxylic acids Flashcards
-COOH
Carboxylic acid
Carboxylic acids are _______ compounds 
Polar
IUPAC  rules for naming unbranched carboxylic acids
-end in -oic acid
-alkanoic acid
EX: methanoic acid
IUPAC rules for naming branch carboxylic acids
- select the longest continuous carbon chain that contains the carboxy group
- Numbers starting at the carbon bearing the carboxylic acid
IUPAC rule for naming carboxylic acids attached to a ring
Name of the ring + Carboxylic acid***
When two are more different functional groups are present in a compound, functional group ________ are used
Priorities (food-chain table)
When using common names, what is the root for one carbon?
Form-
When using common names, what is the root for two carbons?
Acet-
When using common names what is the root for three carbons?
Propion
When using common names, what is the root for four carbons?
butyr-
When using common names, what is the root for five carbons?
Valer-
When using common names, what is the root for six carbons?
Capro-
When using common names for unbranched Carboxylic acid what are the rules?
Root + -ic acid
What is used For the common names for branched carboxylic acids? How are the carbons named?
Alpha (1), beta (2), Gamma (4), Delta(5)
Common name for naming aromatic acids?
Named as benzoic acids
*diacids are acids that contain 2 -COOH Functional groups, IUPAC end in dioic acid, but common names are preferred
- How are carboxylate ions: metal salts, named by IUPAC system?
- What about common name? 
- Name of metal + alkan- + -oate
* Carboxylate —-> Conjugate bases of carboxylic acid - Name of metal + root- + -ate
What is the most polar functional group?
What type of forces do they have? 
Carboxylic acid
What type of forces do carboxylic acids have?
- VDW forces
- dipole dipole forces
- Hydrogen bonding
Carboxylic acids exist as _______
Dimers
Since carboxylic acids have very strong intermolecular forces, they have ___________ BP and MP The other compounds of comparable molar mass
Higher
Call carboxylic acids are __________ In organic solvents
Soluble
Carboxylic acids with a number of carbons less than _____ Are soluble in water.
5
Oxidative cleavage of Alkynes 
Catalysts: O3/H2O or KMnO4/H3O+
Carboxylic acids are produced from internal Alkynes.
For terminal Alkynes, a carboxylic acid and CO2 are produced
What are the products of oxidative cleavage of Alkenes with acidic or neutral KMnO4? 
- if there are hydrogen on the carbons of the double bond, = 2 carboxylic acids
- if there are two hydrogens on a carbon of the double bond, = CO2 and Carboxylic acid is formed 
- There are no Hydro double bond carbons, = 2 ketones
What are the five ways carboxylic acids can react?
-as Bronsted Lowry acids through the O-H bond
-as weak bases with strong in organic acids HA Through the O Of the -C=O group
-As weak bases with strong in organic acids HA Through the O of the -OH group
-
If the first PKA is lower (less stable) Then the second PKA, the reaction…..
Goes as written
The more stable the car boxelite ion, the more ________ Its conjugate carboxylic acid
Acidic
The _________ PKA, The more reactive the acid
Smaller
EWG (halogens), make carboxylic acids more _______ (when not in a ring)
Acidic
They stabilize the carboxylate ion
Are alkyl groups electron withdrawing or electron donating groups?
Electron donating group
Alkyl groups (EDG)…. They \_\_\_\_\_\_\_\_\_\_\_\_ Decarboxylate ion, they make the acid \_\_\_\_\_\_ acidic 
Destabilize, less
The more EDG on the acid, the ______ acidic the acid
Less
What are the electron withdrawing groups of benzoic acids?
EWG= nitrates, halogens, etc.
They stabilize the benzoate ion and make the acid more sick than benzoic acid
What are the electron donating groups of substituted benzoic acids?
EDG= alkyl groups and others (OH?)
- they disable as the benzoate ion, they make the acid less acidic than benzoic acid
why is Tosylic acid a very strong acid?
The conjugate base is resonance stabilized
PKA -1
Why is TsO A very good leaving group?
It is resonance stabilized
what is a zwitterion?
Part is depronated and part of it is protonated
the pI of an aa is the pH at which the amino acid exists mainly as a neutral…..
Zwitterion
D-amino acid is on the _____ .
And an L-animo acid is on the ____.
Right, left