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Org Chem Final Reviewer

This document provides information on carboxylic acid derivatives including their names, properties, preparations, and reactions. It discusses acid chlorides, acid anhydrides, esters, amides, and nitriles. Key points covered include the boiling points and reactivity of these derivatives, nucleophilic acyl substitution reactions, hydrolysis of esters and amides, and reactions of carboxylic acids and esters with Grignard reagents and other organometallic compounds. Triglycerides, fats, and the saponification reaction are also summarized.

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112 views7 pages

Org Chem Final Reviewer

This document provides information on carboxylic acid derivatives including their names, properties, preparations, and reactions. It discusses acid chlorides, acid anhydrides, esters, amides, and nitriles. Key points covered include the boiling points and reactivity of these derivatives, nucleophilic acyl substitution reactions, hydrolysis of esters and amides, and reactions of carboxylic acids and esters with Grignard reagents and other organometallic compounds. Triglycerides, fats, and the saponification reaction are also summarized.

Uploaded by

blessa
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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BLESSA JUDIMIN T. RIVERA  I.U.P.A.C.

Nomenclature
BSCHE2
FINALS REVIEWER

Carboxylic Acid Derivatives

 Acid Chlorides Page


 Acid Anhydrides |1
 Esters
 Amides
 Nitriles

Boiling points of Carboxylic Derivatives

 Acid Chlorides

Reactivity of Acid Derivatives  Acid Anhydrides

Nucleophilic Acyl Substitution  Esters


 Amides  The name of the carboxylic acid of benzene, is
benzoic acid.
 The carbon in the carbonyl group is bonded to .
carbon 1 in the benzene ring.
 The ring is numbered to give the lowest possible
numbers for any substituents. Page
 The prefixes ortho, meta, and para may be used to |2
show the position of one other substituent.

CARBOXYLIC ACIDS. A carboxylic acid contains a hydroxyl


group (–OH) attached to a carboxyl group, which is a
Acidity of carboxylic acids
carbonyl group.

Substituent Effects on Acidity


IUPAC Names of Carboxylic Acids

Salts of Carboxylic Acids


 Sodium hydroxide removes a proton to form the salt.
 The carboxylic acid group needs to be included in the  Adding a strong acid, like HCl, regenerates the
longest chain of carbons. carboxylic acid.
 The carbon of the carboxylic acid group is given the
number 1 (since it is on the end of a chain)
 The suffix becomes anoic acid.
PREPARATION OF CARBOXYLIC ACIDS EXAMPLES

1.) Grignard Synthesis


 The carbonation of Grignard reagents
 Grignard reagent + CO2 yields a carboxylate salt.
Page
|3

--------------------------------------------------------------------------
REACTIONS OF CARBOXYLIC ACIDS
1. Carboxylic acid reacts with thionyl chloride to form
acyl chloride

2.) Hydrolysis of Nitriles


 Basic or acidic hydrolysis of a nitrile produces a
carboxylic acid. 2. Carboxylic acid is reduced to alcohol using LiAlH4
 Nitriles, also known as alkyl cyanides, are prepared Carboxylic acids are reduced to primary alcohols by
by nucleophilic substitution the powerful reducing agent lithium aluminum
hydride.

3. Saponification
4. Esterification reaction
ORGANOMETALLIC REAGENTS Some Carbonyl Compounds
 The organomagnesium halides (RMgX), known
as Grignard reagents, are useful synthetic
intermediates in organic chemistry for carbon-
carbon bond formation.
Page
Reactions of RMgX with Carbonyl Compounds |4
Being nucleophilic in nature, the organomagnesium
halides undergo 1,2-addition to the carbonyl group of
formaldehydes,aldehydes, ketones, esters, anhydrides,
acid chlorides and amides

-------------------------------------------------------------------------
TRIGLYCERIDES AND FATS
Triglycerides
 are the most common component of edible fats and
oils
 are triesters of the alcohol glycerol, (propane-1,2,3-
triol) and fatty acids
--------------------------------------------------------------------------
NUCLEOPHILIC ACYL SUBSTITUTION
A “nucleophilic addition reaction” (of a carbonyl
compound) involves the initial attack of a nucleophile on
the slightly positive carbonyl‑carbon atom to form a
tetrahedral intermediate.
In a “nucleophilic acyl substitution reaction,” a Saponification
nucleophile attacks the carbonyl carbon of a carboxylic  alkaline hydrolysis of triglycerol esters produces
acid derivative and initially produces a soaps
tetrahedral intermediate. The intermediate  a simple soap is the salt of a fatty acid
then reacts by expelling the leaving group, X, thereby  as most oils contain a mixture of triglycerols, soaps
forming a new carboxylic acid derivative. are not compounds
The following scheme illustrates the relative  the quality of a soap depends on the oils from which
reactivities of most carboxylic acid derivatives it is made
MECHANISM OF BASE PROMOTED ESTER HYDROLYSIS

MECHANISM OF THE BASE HYDROLYSIS OF ESTERS


Page
|5
Step 1:
3.) Addition of Grignard reagents convert esters to 3o
The hydroxide
alcohols. In effect the Grignard reagent adds twice.
nucleophiles attacks at
the electrophilic C of the
ester C=O, breaking the π
bond and creating the
tetrahedral intermediate
Step 2:
The intermediate
collapses, reforming the
C=O results in the loss of
the leaving group the
alkoxide, RO-, leading to
the carboxylic acid. -------------------------------------------------------------------------
Step 3: PREPARATION OF AMIDES
An acid / base reaction. A 1.) Reaction of carboxylic acids and amines
very rapid equilibrium
where the alkoxide,RO-
functions as a base
deprotonating the 2.) Reaction of Acyl Chloride and amines
carboxylic acid, RCO2H,
(an acidic work up would
allow the carboxylic acid
to be obtained from the
reaction).
------------------------------------------------------------------------ 3.) Reaction of Acid Anhydrides and amines
REACTION OF ESTERS

1.) Hydrolysis. Esters can be cleaved back into a


carboxylic acid and an alcohol by reaction with
water and a catalytic amount of acid. --------------------------------------------------------------------------
Hydrolysis of amides into carboxylic acids
Technically, hydrolysis is a reaction with water. That is
exactly what happens when amides are hydrolyzed in the
presence of dilute acids such as dilute hydrochloric acid.
The acid acts as a catalyst for the reaction between the
amide and water. The alkaline hydrolysis of amides
actually involves reaction with hydroxide ions, but the
result is similar enough that it is still classed as hydrolysis.
2.) Reduction. Esters can be converted to 1o alcohols
using LiAlH4, while sodium borohydride ( NaBH4 ) is
not a strong enough reducing agent to perform this
reaction.
Hydrolysis of amides into carboxylic acids With Acidic & Basic Side Chains

Page
|6

Isoelectric Point
 pH at which an amino acid, polypeptide, or protein
-------------------------------------------------------------------------- has a total charge of zero.
 The pI for glycine, for example, falls between the
AMINO ACIDS pKa values for the carboxyl and amino groups

Amino Acids with Nonpolar side chains

Electrophoresis
 The process of separating compounds on the basis of
With Polar side chains their electric charge.
 electrophoresis of amino acids can be carried out
using paper, starch, polyacrylamide and agarose
gels, and cellulose acetate as solid supports.
Polypeptides & Proteins

Page
|7

Writing Peptides

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