Carboxylic Acids Derivatives - Chp 21 Flashcards
How to name acyl halides?
Replacing -ane with -yl
ex. ethanoyl fluoride
How to name anhydrides?
add “anhydride” to the end
ex. C4H6O3 is acetic anhydride
Esters are named as alkyl carboxylates. How do you name them?
Add -oate
ex. phenyl benzoate
Cyclic esters are called _______ and named by adding ________.
lactones; acid lactone
ex. 5-hydroxypentanoic acid lactone
How to name amides?
Replace -ic or -oic with -amide.
ex. N-ethylethanamide
Cyclic amides are called _____. How to name them?
Lactams; Add “acid lactam”
ex. 4-aminobutanoic acid lactam
How to name nitriles?
Add -nitrile to the alkane name.
ex. ethanenitrile
What determines the parent name of a compound?
The functional group with the highest priority.
List the order to priority for the given groups:
Acid
Nitrile
Amide
Aldehyde
Ketone
Alkene
Alkane
Amine
alcohol
Ester
ether
carboxylic acid
carboxylic acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine > alkene, alkyne > ether
You add ___ for carboxylic acids, ____ for esters, ____ for aldehydes, ___ for ketones, ___ for alcohols, ______ for amides and ______ for nitriles.
-oic acid; -oate; -al; -one; -ol; -amide; -nitrile
Do amides have very high b.ps & m.ps compared to other compounds of similar weight?
Melting points _______ with increasing # of _____ bonds.
Yes; increase; N-H
List the order of reactivity from most to least with the following functional groups: ester, carboxylate, amide, anhydride, acid chloride
Acid chloride, anhydride, ester, amide, carboxylate
List the order of increasing basicity with the following leaving groups: OR, NH2, Cl, COOR,
Cl, COOR, OR, NH2
Will a reaction occur if the product is more reactive than the reactants?
No.
Carboxylic acid –> acid chloride
SOCl2 or COCl2
Anhydride means without water. So removing 1 mole. of water from 2 mole.s of carboxylic acids forms _______.
an anhydride
An acid chloride + an acid forms ___________. What attacks what?
an anhydride; OH from acid attacks the carbonyl on acid chloride.
Acid + alcohol forms ______. What attacks what?
ester; Alcohol attacks carbonyl.
Anhydride + alcohol forms _______. What attacks what?
ester and acid (COOH); Alcohol attacks carbonyl of anhydride
Acid chloride + _________ forms an amide.
2 amines (NHR2)
Anhydride + amine forms ______.
amide
Ester + ______ forms amide.
primary amine or NH3
Nitrile + H2O (or H+ or -OH) forms ______, then + H2O and H+ forms ______.
Primary amide; carboxylic acid
Carboxylic acid + NH3 and heat forms _____, then + POCl3 forms _______.
primary amide; nitrile
Acid chloride + H2O forms _______.
carboxylic acid
Amide + H3O forms _____. (Acid hydrolysis)
an acid
Ester + LiAlH4 forms ________, then + H3O+ forms ________.
a primary alkoxide; primary alcohol
Acyl chlorides + LiAlH(O-t-Bu)3 forms _______.
an aldehyde
Ester reacting with 1) DIBAL [(i-Bu)2AlH] 2) H2O forms _______.
an aldehyde
What reduces an amides to an amine? (Primary, secondar and tertiary) What attacks what?
1) LiAlH4 2) H2O (Same for all three); H from AlH4 attacks carbonyl
Nitrile to primary amine needs what reagent?
H2/Pt or 1) LiAlH4 2) H2O
Ester + 2C4H9Li and H3O+ forms _______.
secondary alcohol
Acid chloride + 2Grignard and H3O+ forms _______.
a tertiary alcohol
Ester + Grignard reagent forms _______, then + Grignard reagent forms ______.
a ketone; an alcohol
Nitrile + Grignard and H3O+ forms _______.
a ketone
List in increasing order for boiling point for the following groups: ester, amide, alkane, nitrile, acid and alcohol
alkane, ester, nitrile, alcohol, acid, amide
Acid chloride + amine (NH2) forms ______.
an amide
Acid chloride + an alcohol forms ______.
an ester
Amide + 1) LiAlH4 2) H2O forms ______.
an amine (takes out the carbonyl C=O)
Ester + NaOH (saponification) forms _______.
carboxylate and an alcohol
Nitrile + NaOH (or -OH) and H2O forms _________, twice (again) forms ______.
a primary amide; carboxylate ion and NH3
Ester + 2 R’‘MgX and H2O forms ____________.
A tertiary alcohol.
