Chapter 20 & 21 Reaction Chart Carboxylic acids and derivatives

-Chapter 20 and 21 deals with reaction/synthesis of carboxylic acids and its derivatives. There are essentially 5
different derivatives of carboxylic acid: Acid Chlorides, Anhydrides, Esters, Amides, and Nitriles. Essentially,
the majority of the reactions covered in this chapter are interconverting into the different derivative
forms, with the rest of the reactions mostly review from previous chapters. Again, there are 2 general mechanisms
for a Carboxylic acid/derivate reaction: The Acid catalyzed mechanism, and the Basic Catalyzed mechanism, which
are both shown below.
-The Basic catalyzed mechanism is primarily utilized for Acid Chlorides and Anhydrides. Since the
substituent attached to the acyl group (Cl or carboxylate ion) are good leaving groups, it makes the
Acid Chloride and Anhydride good electrophiles so that the nucleophile can directly attack the carbonyl
carbon without having to protonate the oxygen to make it more electrophilic. In this reaction, an acid
chloride is reacting with an alcohol. Once it attacks, a tetrahedral intermediate will form, with an alkoxide, chloride,
an alcohol as substituents on the carbonyl carbon. Now, at this point, the most stable leaving group will be
kicked off. In this case, Chloride is the most stable leaving group, so it will leave, with the oxygen reforming the
carbonyl group. Chloride will then extract a hydrogen, and an ester will form.

-In the acid catalyzed mechanism, the main difference is that the carbonyl oxygen is first protonated to
make it a better electrophile. Therefore this mechanism typically occurs for Esters, Amides, and
Carboxylic acids, which are less reactive than Acid Chlorides and Anhydrides. Once the oxygen is
protonated, the nucleophile will attack, and a tetrahedral compound will form.

In this case, the OH will be protonated to form water, and will be kicked off. The oxygen will reform the
carbonyl again, and a hydrogen will be extracted to form the ester.

-Below is a diagram from the book that shows the reactivity of the carboxylic acid derivatives. The reactivity of
the carboxylic acid/derivate is dictated by the substituent attached on the acyl group. The more stable
the leaving group is on the carboxylic acid derivative, the faster the reaction will occur in a nucleophilic
substitution reaction. The leaving group of an acid chloride is a chloride ion, which is a very weak base, and is
very stable by itself. Therefore, it will readily be kicked off, and will be the most reactive carboxylic acid derivative.
Essentially, carboxylic acid derivates can ONLY react to form less reactive derivatives. Therefore, though
an Acid Chloride can directly convert to an amide, an Amide cant be directly converted into an acid chloride since
the amine ion is much more reactive than a chloride ion. Know this reactivity chart really well! You may be
asked to rank carboxylic acid derivatives by their reactivity, which is dictated by the stability of their
leaving group! It is also very important to consider when approaching reaction questions!

Below I have drawn a general flowchart of the conversion of the various forms. This is probably the
most important aspect of Chapter 20 & 21, so know which derivatives can be converted to which
another form and the reagents needed to perform the reaction! Basically, if you want to form an acid
chloride, use SOCl2. If you want to form an anhydride, add a carboxylic acid. If you want to form an
ester, add an alcohol. If you want to form an amide, add an amine, and if you want to reform a
carboxylic acid, add water and H+.

-There are many review reactions from previous Chapters that are on this chart. You should already have a good
understanding of those reactions, so I will try to emphasize the new reactions you should know.
Synthesis of Carboxylic acids
Reaction

Example (Mechanism)

Oxidation
of Primary

-From Chapter 11, a primary alcohol can be oxidized with a chromium

reagent, which will first oxidize the alcohol to an aldehyde. However,

Reactants, Reagent,
Products
Reactant Primary
Alcohol or

Important things to
note
- Wont be directly
asked this, but know

alcohols/al
de-hydes
(Ch 11)

since chromium is a strong oxidizing agent, it will continue to oxidize

the aldehyde into a carboxylic acid.

aldehydes
Reagent: A
Chromium (VI)
reagent Cr(VI)
(Na2Cr2O7, or CrO3 in
H2SO4), or KMnO4
Product A
carboxylic acid

this reaction
because it is useful
for synthesis
questions!

Oxidative
Cleavage
of Alkenes
(Ch 8)

-From O.Chem 1, an Alkene can react with warm, acidic, and

concentrated KMnO4 to form ketones/aldehydes. Any aldehydes
present will oxidize further to carboxylic acids.

Reactant- An Alkene
Reagent Warm,
acidic, or
concentrated
KMnO4
Product Mixtures of
ketones, or
carboxylic acids

- Shouldnt be asked
this, know in case,
specifically for
synthesis questions!
-Remember, the
permangate has to be
in warm,
concentrated, or
acidic conditions to
form
ketones/carboxylic
acids

Oxidation
of alkynes
(Ch 9)

-From O.Chem 1, an alkyne can react with warm, basic, concentrated

KMnO4 to cleave the triple bond to form carboxylate salts, which can
be protonated to form carboxylic acids

Reactant An Alkyne
(terminal or
internal)
Reagent: Warm,
basic, concentrated
KMnO4 or O3 and
H2O
Product: Multiple
Carboxylic acids

- Shouldnt be asked
this, know in case,
specifically for
synthesis questions!
- Warm,
concentrated, and
basic, NOT acidic
KMnO4 is needed to
form carboxylic acid

Reactant- Benzene
ring with carbon

- Wont be directly
asked this, but know

-An alkyne can also react with ozone and H2O that will cleave the
triple bond to form 2 carboxylic acids as well

Oxidation
of

-Remember from Ch 17 that KMnO4 or hot chromic acid can be used

to oxidize carbon groups on benzene rings to carboxylic acids. Only

alkylbenze
ne (Ch 17)

alkane carbon groups will react, any other group will not be reacted!

(alkane) substituents
Reagent KMnO4,
NaOH (basic
conditions), or
Chromic acid and
heat
Product carboxylic
acids on benzene
rings

this reaction
because it is useful
for synthesis
questions!
-Will oxidize any
adjacent carbon
group (alkyl groups,
carbonyl groups, etc)

Carboxyla
tion of
Grignard
reagent

Remember from O.Chem 1 that Grignard reagents are very strong

nucleophilies. Therefore, a Grignard reagent can react with CO 2, and
can form a carboxylic acid.

Reactant: A Grignard
reagent (R-MgBr)
Reagent: Carbon
dioxide (CO2)
Product: A carboxylic
acid

-Know this reaction!

Not really a new
reaction, but a good
reaction to synthesis
carboxylic acids
with.

Hydrolysis
of Nitriles
(Ch 18)

-Nitriles (-CN) can be hydrolyzed under acidic conditions. The nitrile

will first be hydrated to form an amide, which will be hydrated again
to form a carboxylic acid.

Reactant: A Nitrile
(R-CN)
Reagent: H+ and H2O
Product: A Carboxylic
acid

-Know this reaction!

It is a useful
reaction for
converting cyanides
to carboxylic acids

Reactants, Reagent,
Products
Reactant Carboxylic
acid
Reagent: An Alcohol
in acidic conditions
Product Ester, with
the alcohol R group
attached to the O

Important things to
note
-Know this reaction
and the mechanism!
It essentially follows
the acid catalyzed
mechanism.
-Remember, the
carboxylic acid has
to be reacted in
acidic conditions to
protonate the

Reactions of Carboxylic Acids

Reaction
The
Fischer
Esterifica
tion (Ch
11)

Example (Mechanism)
-A carboxylic acid can be reacted with an alcohol. Since the
carboxylic acid is not a good electrophilie, it will be protonated first
to make it more electrophilic. After protonation, the alcohol will
attack, and a tetrahedral intermediate will form

oxygen to make it
more electrophilic!

-One of the alcohols will be protonated, leaving as water, forming an

ester with the alcohol attached to the carbonyl carbon.

The overall reaction is shown below

Esterficat
ion using
Diazomet
hane

-A carboxylic acid can react with Diazomethane (Diazonium with a

methyl attached) to form an ester. The negatively charged carbon will
first extract the carboxylic acid hydrogen, now forming a negative charge on
the oxygen, which will then attack the methyl group, with N 2 leaving, forming
the ester.

Reactant- Carboxylic
acid
Reagent
Diazomethane
(CH2N2)
Product An ester,
with the methyl
group attached to
the oxygen

-Dont need to know

the mechanism, but
know the reaction!
-Usually only uses
diazomethane (CH3N2).

Direct
synthesis
of Amides
(Ch 19)

-Similar to the reaction of the diazomethane, the carboxylic acid

hydrogen will first be extracted by the amine, forming the
carboxylate ion. Under heated conditions, this will react with the
amine to form an amide.

Reactant: Carboxylic
acid
Reagent: An amine
(can be ammonia,
primary or
secondary), and
heat
Product: An Amide,
with the amine

-Dont need to know

the mechanism, but
know the reaction!
-Usually better to
convert carboxylic
acid to an acid
chloride, then form
the amide

replacing the OH

Reduction
of
Carboxylic
Acids to
alcohols
(Ch 10)

-Though a carboxylic acid can be converted straight to an amide, it is

usually preferred to convert the carboxylic acid to an acid chloride,
then to the amide since weaker conditions can be used
-Remember that carboxylic acids can react with LAH to form primary
alcohols. The first addition will actually form an aldehyde, and the
second addition will form the primary alcohol.

Reactant- Carboxylic
acids
Reagent LiAlH4
(LAH) or BH3*THF
Product Primary
alcohols

- Dont need to know

the mechanism, but
know the reaction!
-Remember, LiAlH4 is
reactive, not
selective, while
BH3*THF is selective
for carboxylic acids

Reactant: Carboxylic
acids
Reagent: SOCl2 or
(COCl)2
Product: Acid
chlorides

-Dont need to know

the mechanism, but
know the reaction!
-One of the only
reactions to form
acid chlorides! They
are the most reactive
carboxylic acid
derivatives, and
essentially form every
single carboxylic acid
derivative.
-SOCl2 can only be
reacted on
carboxylic acids to

- BH3*THF can also be used to reduce carboxylic acids to primary

alcohols, but will preferentially react with carboxylic acids over any
other carbonyl group. Therefore, with only 1 addition, will only
reduce the carboxylic acid

Synthesis
of Acid
Chlorides

-Acarbonyl oxygen of the carboxylic acid can react with SOCl 2 to form a
resonance stabilized compound shown below

-The chloride will then leave, and the carbonyl on the sulfur will reform, with
the chloride extracting a hydrogen from the carbonyl oxygen, forming a
chlorosulfite anhydride

form acid chlorides.

It will not work with
anhydrides, esters,
and amides!

-Chloride will then attack the anhydride, preferentially the carbon instead of
the sulfur. The ester substituent will then be removed, now forming the acid
chloride. You dont need to know the mechanism!

-The overall reaction is shown below

Reduction
of
carboxylic
acids to
aldehydes
(Ch 18)

There is no direct way to convert a carboxylic acid into an aldehyde.

It must be converted to an acid chloride first by reacting a carboxylic
acid can be reacted with SOCl2 to attach a chlorine on the carbonyl
carbon.

The acid chloride can then be reduced by Lithium tri- tertbutoxyaluminum hydride (LiAlH(O-t-bu)3). This is a weaker reducing
agent than LAH, so will only reduce the acid chloride to the aldehyde and not
the alcohol. Notice that this only forms aldehydes, not ketones!

Reactant: An acid
chloride (can be
generated by adding a
carboxylic acid with a
thionyl chloride
(SOCl2)
Reagent: Lithium tritertbutoxyaluminum
hydride (LiAlH(O tBu)3)
Product: An
aldehyde,

-Dont need to know

the mechanism, but
know the reaction!
-LiAlH(O t-Bu)3 is a
weaker reducing agent
and can reduce the
acid chloride to the
aldehyde form, while
LiAlH4 would reduce it
all the way to an
alcohol

Alkylation
of
Carboxylic
Acids to
form
ketones
(Ch 18)

From Ch 18, to convert a carboxylic acid into a ketone, 2 additions of

a organolithium are needed (any R group can be used for the
organolithium compound). The first organolithium reagent is used to
deprotonate the acidic carboxylic hydrogen to form a carboxylate ion. The
second addition will be used to form a dianion.

onation of the dianion will cause a dehydration, and reformation of the

carbonyl, now forming a ketone

Prot

Reactant- A
carboxylic acid
Reagent 2
organolithium
compounds (any R
group can be used).
Notice that in the first
deprotonation, a
weaker base such as
OH can be used
Product A ketone
with another R
group attached
replacing the OH.

-Dont need to know

the mechanism, but
know the reaction!
Keep in mind you
need 2
organolithium
reagents to form the
ketone!
-One of the only
reactions that
directly converts an
carboxylic acid to a
ketone

Reactants, Reagent,
Products
Reactant An Acid
Chloride
Reagent: Depends on

Important things to
note
- Know this reaction
and the mechanism!
-Essentially follows

The overall reaction is shown below

Reactions involving Acid Chlorides

Reaction
Interconv
ers-ions
of Acid

Example (Mechanism)
-Remember that acid chlorides react under basic catalyzed
mechanisms since they are more reactive than other derivatives.
Therefore, nucleophilies can directly attack the carbonyl carbon

Chloride
to
Carboxyli
c acid
derivativ
e
(anhydrid
e, ester,
amide,
carboxyli
c acid)

without protonation of the oxygen. Below are different reactions of

acid chlorides to convert to different carboxylic acid derivatives.
-Acid chloride can react with with a carboxylic acid (or carboxylate
ion), forming a tetrahedral intermediate, and the loss of chloride, forming
an anhydride

-If an Acid chloride reacts with an alcohol, it will follow the same
mechanism, with the Cl leaving, forming an ester

-If an Acid chloride reacts with an amine, it will form an amide

-Acid chlorides can also react with water (no acidic conditions
needed), to reform carboxylic acid.

what derivative is
formed
-Formation of
anhydride
carboxylic acid or
the salt form
-Formation of an
ester an alcohol
-Formation of an
amide ammonia,
primary or
secondary amine
-Formation of a
carboxylic acid
water
Product Anhydride,
ester, amide, or
carboxylic acid

the basic catalyzed

mechanism, where
the nucleophile
attacks first, forms
the tetrahedral
intermediate, and
kicks off chloride
-Remember the
reactivity chart!
Since acid chlorides
are the most
reactive, with Cl
being a good leaving
group, it can
interconvert to all
the different
derivatives:
anhydrides, ester,
amide, or carboxylic
acid again.

Reduction
of Acid
Chlorides
(Ch 10, 18)

Acid chlorides can be reduced by different reagents to form different

products, all listed below.
-The acid chloride can then be reduced by Lithium tri- tertbutoxyaluminum hydride (LiAlH(O-t-bu)3). This is a weaker reducing
agent than LAH, so will only reduce the acid chloride to the aldehyde and not
the alcohol. Notice that this only forms aldehydes, not ketones!

-If LiAlH4 is used, it will reduce the acid chloride all the way to a primary
alcohol. Remember LAH adds twice, with the first time forming the aldehyde,
and the second forming the alcohol.

Reactant An acid
chloride
Reagent:
Formation of an
aldehyde - (LiAlH(O
t-Bu)3
Formation of an
alcohol - LAH
-Formation of a
ketone R2CuLi
Product: An
aldehyde, alcohol,
or ketone

- Dont need to know

the mechanism, but
know the reaction!
-The strength of the
reducing agent
dictates the product
form. A weaker
reducing agent such
as the hindered LAH
will only form the
aldehyde, while
unhindered LAH will
react to reduce the
acid chloride all the
way to an alcohol

Reactant: An Acid
Chloride
Reagent: Grignard
reagent (R-MgBr)
Product: A tertiary
alcohol, with 2
additions of the
Grignard reagent

-Dont need to know

the mechanism, but
know the reaction!
-A ketone will form
with 1 equivalent
addition, but an
additional
equivalent will form
the 3o alcohol with 2
additions of
grignards

-To convert an acid chloride into a ketone, A lithium dialkylcuprate

(Gilman reagent) is needed to add an R group to the acid chloride.
Notice that 2 R groups are attached to the reagent in order for just one to
attach onto the carbonyl to form the ketone

Grignard
reactions
of acid
chlorides
(Ch 10)

-An acid chloride will react with a Grignard reagent 1 time to form a
ketone, which will react again with the Grignard reagent for form a
tertiary alcohol, with 2 additions of the Grignard on the carbonyl
group. A tertiary alcohol is always formed, with 2 additions of
Grignards!

Reactions involving Anhydrides

Reaction
Formatio
n of a
cyclic
anhydrid
e

Example (Mechanism)
-Under acidic conditions, a compound with 2 carboxylic acids in a
chain can cyclize. One of the carbonyl oxygens will get protonated,
allowing for the opposite carboxylic acid to attack the more
electrophilic carbon, forming a cyclic tetrahedral shown below.

-Under acidic conditions, one of the alcohols will get protonated, and
leave as water, reforming the carbonyl and forming the cyclic
anhydride

-The cyclic anhydride can react with a nucleophile, breaking the ring and
reacting with 1 side of the carboxylic acid, forming unsymmetrical carboxylic
acid derivative compounds. Notice that the side that kicks off the most
stable leaving group is reacted. The carboxylic acid with the
fluorines attached is more stable because it helps to stabilize the
excess electron density

Reactants, Reagent,
Products
Reactant A
dicarboxylic acid
Reagent: Acidic (H+)
conditions
Product A cyclic
anhydride (2
carbonyl groups
adjacent to a cyclic
O), which can be
reacted further to
form multiple
carboxylic acid
derivatives

Important things to
note
- Know this reaction
and the mechanism!
You will be given
several questions
that involves the
formation of cyclic
carboxylic acid
derivatives!

Interconv
ersi-on of
Anhydrid
es to
other
carboxyli
c acid
derivativ
es
(esters,
amides,
and
carboxyli
c acids)

-Like acid chlorides, an anhydride reacts in a basic catalyzed

mechanism involved a direct nucleophilic attack onto the
electrophilic carbon, forming the tetrahedral intermediate, and
kicking off the carboxylate ion, forming the new carboxylic acid
derivative.

-Besides being able to react with an alcohol to form an ester,

anhydrides can react with an amine, to form an amide.

-Anhydrides can also react with water, to form 2 carboxylic acids. The other
carboxylic acids is not drawn below

Reactant: Anhydride
Reagent:
-Formation of an
ester an alcohol
-Formation of an
amide ammonia,
primary or
secondary amine
-Formation of a
carboxylic acid
add water
Product: ester,
amide, or carboxylic
acid

- Know this reaction

and the mechanism!
-Essentially follows
the basic catalyzed
mechanism, where
the nucleophile
attacks first, forms
the tetrahedral
intermediate, and
kicks off a
carboxylate ion
-Remember the
reactivity chart!
Since anhydrides are
less reactive than
acid chlorides,
anhydrides are
unable to be directly
converted to an acid
chloride. It can only
react with a
nucleophile that
forms a less stable
carboxylic acid
derivate. Therefore,
it can only react with
alcohols, amines,
and water to form
esters, amides, and
carboxylic acids!

Reactions with Esters

Reaction

Example (Mechanism)

Interconv
ersi-on of
esters
(amides,
carboxyli
c acids

-An ester can react with an amine in an acid catalyzed mechanism.

The ester will be protonated first to form a more electrophilic
compound. Then the amine can attack the carbonyl carbon, forming
the tetrahedral intermediate below. The alcohol will then be kicked
off (it will be protonated first, then leave, not shown below), forming
the amide.

Reactants, Reagent,
Products
Reactant An ester
Reagent:
-Formation of an
amide ammonia,
primary or
secondary amine
-Formation of a
carboxylic acid H+
and H2O

Important things to
note
-Know this reaction
and the mechanism!
-Essentially follows
the acidic catalyzed
mechanism, where
the nucleophile
attacks first, forms
the tetrahedral
intermediate, and

Product either an
amide or a
carboxylic acid

kicks off an alcohol

-Esters are relatively
unreactive. They can
react to form only
amides, carboxylic
acids, and other
esters, which is
shown below.

-An ester can react with acidic water, forming the similar tetrahedral
intermediate. The alcohol will then leave (protonated first), and
then form the carboxylic acid

Transeste
rfic-ation
(switch R
groups
on an
ester)

-An ester can react with an alcohol under acidic conditions, to form a new
ester, with a different substituent attached to the alcohol. It will undergo the
same acid-catalyzed mechanism, form the tetrahedral intermediate, and kick
off the initial alcohol attached

Reactant An ester
Reagent: An alcohol
and H+
Product: An ester,
with a different R
group attached to
the oxygen atom

- Know this reaction

and the mechanism!
-The easiest way of
switch a R group on
an ester
-Essentially follows
the acidic catalyzed
mechanism, where
the nucleophile
attacks first, forms
the tetrahedral
intermediate, and
kicks off an alcohol

Reaction
of
thiolester
s

-A thiolester (S instead of O), has very similar reactivity to an ester. It is

actually more reactive than an ester and amide, but less reactive
than an acid chloride and an anhydride. Therefore, a thiolester can
be converted into an ester, amide, or carboxylic acid. It will follow a
similar mechanism of an ester. Below is a thiolester reacting with an amine,
forming an amide

Reactant An
thiolester
Reagent:-Formation
of an ester an
alcohol
-Formation of an
amide ammonia,
primary or
secondary amine
-Formation of a

-Know this reaction

and the mechanism!
It is essentially the
same as an ester,
but with a sulfur
instead of a oxygen
-Thiolsulfurs are
more reactive than
esters, but less
reactive than

Reaction of
Grignards
to esters,
and
reduction
of esters

-Similar to acid chlorides, esters can react with Grignard reagents twice,
similar to acid chlorides, to form a tertiary alcohol with 2 addition of Grignards

-Similar to Carboxylic acids, esters can react with LAH to form primary
alcohols. Two additions of LAH are needed to form the primary alcohol

carboxylic acid
add water
Product: An ester,
amide, or carboxylic
acid

anhydrides and acid

chlorides.

Reactant An ester
Reagent:
-Formation of 3o
alcohol Grignards
-Formation of 1o
alcohol - LAH
Product: An ester,
with a different R
group attached to
the oxygen atom

-Dont need to know

the mechanism, but
know the reaction!
-Know these reaction
for synthesis
questions, just in
case

Reactions involving Amides

Reaction

Example (Mechanism)

Reactants, Reagent,
Products
Reactant An Amide
Reagent: H+ and
water
Product Carboxylic
Acids

Important things to
note
- Know this reaction
and the mechanism!
- Cant directly
convert to an acid
chloride, anhydride,
thiolester, or ester!
Can only be
converted into a
carboxylic acid

Hydrolysi
s of
Amides
(forms
Carboxyli
c acid)

-Amides are the least reactive out of all of the carboxylic acid derivatives.
Therefore, an amide cant directly convert to an acid chloride,
anhydride, thiolester, or ester. It can be converted back to a
carboxylic acid through an acid catalyzed mechanism that requires
the protonation of the carbonyl oxygen. After formation of the
tetrahedral intermediate, the amine will get kicked off, forming the
carboxylic acid.

Dehydratio
n of
Amides to
Nitriles

-Primary amides can be dehydrated using a strong dehydrating

agent such as POCl3 or P2O5 to form a nitrile. Amides are the only
carboxylic acid derivative that can convert into an nitrile

Reactant Amide
Reagent: - POCl3 or
P2O5
Product: A nitrile

- Dont need to know

the mechanism, but
know the reaction!
- The only carboxylic
acid derivative that
can convert into an
nitrile

From Ch 19, Primary, Secondary or tertiary amides can be reduced

by LiAlH4 to form an amine

Reactant Amide
Reagent: - LAH, or
NaOH, and a
halogen
Product: Amines

- Dont need to know

the mechanism, but
know the reaction!
-See the chapter 19
chart for more
information. Again the
mechanism is not
important, just know
the reagents, what
they do and what is
formed

Review
reactions
of amides
(Ch 19)

-Primary amides can also react with halogens, -OH and water, which
undergoes a rearrangement of the carbonyl substituent so that it
then attaches to the amine, forming a substituted amine. See the Ch
19 chart for more details on the mechanism

Reactions with Nitriles

Reaction

Example (Mechanism)

Hydrolysis
of Nitriles
(forming
Carboxylic
acids)

-Nitriles can react under acidic hydrolysis to form carboxylic acids. Under
weak conditions, it will only go to the amide form, but under strong
conditions or acidic), will continue to go to the carboxylic acid form

Review
reactions
of Nitriles
(Ch 19)

-From Ch 19, Nitriles can react with LiAlH 4 to form amines

-Nitriles can also react with Grignards forming an imine first, but
with further reaction under acidic conditions, will form a ketone

Reactants, Reagent,
Products
Reactant A nitrile
Reagent: H+ and
water
Product Carboxylic
Acid

Important things to
note
-Dont need to know
the mechanism, but
know the reaction!
-When doing this
reaction, will usually
always go to form
the carboxylic acid!

Reactant A nitrile
Reagent:
-Formation of an
Amine LAH
-Formation of a
ketone Grignards,
then H+
Product Amine or
Ketone

-Dont need to know

the mechanism, but
know the reaction!
-See Ch 19 notes for
more details