Exam 2 - Carboxylic Acids Flashcards
In ___, a carboxylic acid can react with 1) NaOH 2) alkyl halide in order to form an ester.
O-Alkylation
In Pinnick Oxidation, an aldehyde + ___, ___ will produce a carboxylic acid.
NaClO2, NaH2PO4
___ - No double bond to N.
amine
A carboxylic acid can react with ___ to make an acid chloride.
SOCl2 (thionyl chloride)
In Pinnick Oxidation, an aldehyde + NaClO2, NaH2PO4 will produce a ___ ___.
carboxylic acid
In Ozonolysis, an alkene + 1) O3 2) H2O2 will produce ___ ___ ___.
two carboxylic acids
*Note, a carboxylic acid can react with ___ to make a primary alcohol.
LiAlH4
Amides have a better resonance structure because ___ is ___ ___, so the positive charge on it is okay.
N is less electronegative, so the positive charge on it is okay
In the Grignard Reaction with Dry Ice, an alkyl halide can react with 1) Mg 2) CO2(s) 3) H3O+ in order to produce a ___ ___.
carboxylic acid
___ and ___ ___ determine carboxylic acid reactivity.
Resonance and LG Ability
imine - ___ ___ ___ ___.
imine - Double bond to N
Jones’ Oxidation can also be used with an aldehyde in order to produce a ___ ___.
carboxylic acid
The better the LG, the more ___ the carboxylic acid.
better the LG = more reactive
In Jones’ Oxidation, a primary alcohol + CrO3, H2SO4, and H2O will produce a ___ ___.
carboxylic acid
Order of reactivity of carboxylic acid derivatives (from most reactive to least reactive):
acid chlorides > acid anhydrides > aldehydes > ketones > esters = carboxylic acids > amides > carboxylates
___ ___ can become all other carboxylic acid derivatives.
acid chlorides
Grignard Reaction with Dry Ice will ___ ___ ___.
add 1 carbon (from CO2)
The ___ the LG’s conjugate acid pka, the better the LG is.
lower
Acid Anhydride has a poor resonance structure due to having ___ ___ ___ near each other.
two positive charges near each other = bad resonance structure
In the Grignard Reaction with Dry Ice, an alkyl halide can react with 1) ___ 2) ___ 3) ___ in order to produce a carboxylic acid.
1) Mg 2) CO2(s) 3) H3O+
A carboxylic acid can react with diazomethane (CH2N2) to make a ___ ___.
methyl ester
*Note, an ylide can not only be stabilized by a nextdoor carbonyl group, an ylide can also be stabilized by ___ ___ ___.
frequent non-carbonyl conjugation
In ___ ___, an aldehyde + NaClO2, NaH2PO4 will produce a carboxylic acid.
Pinnick Oxidation
___ with a ___ ___ will not lose carbons.
Ozonolysis with a cyclic alkene will not lose carbons
