Reagents 2021 LETEST

Reagents in Organic Synthesis
Prepared
By
Dr. Hitesh D. Patel
Professor,
Department of Chemistry,
Gujarat University,
Ahmedabad
12/19/2023 Dr. Hitesh D. Patel 1

Unit 4
Reagents in organic synthesis
• Total 10 reagents, mechanism, selectivity and utility of following reagents:
• 1. HATU
• 2. Lithium diisopropylamide (LDA)
• 3. Dicyclohexyl carbodiimide (DCC)
• 4. 1,3 – Dithiane (Umpolung reagent)
• 5. Dess- Martin periodinane
• 6. Diisobutylauminium hydride( DIBAL –H)
• 7. Sodium cyanoborohydride (NaBH3(CN))
• 8. DDQ
• 9. n-Butyl lithium
• 10. Phase transfer catalysis : Quaternary ammonium and phosphonium
salts, crown ethers.

Substrates
• (1) A chemical species of particular interest,

the reaction of which with some other
chemical reagent is under observation (e.g. a
compound that is transformed under the
influence of a catalyst).
• (2) The chemical entity whose conversion to a
product or products is catalyzed by an
enzymes.

Reactants
• Substances initially present in a chemical
reaction that are consumed during the
reaction to make products.

• Definition of Catalyst
• A substance that speeds up a chemical
reaction, but is not consumed by the reaction;
hence the catalyst can be recovered
unchanged at the end of the reaction it has
been used to speed up, or catalyze.

• Reagent
• A chemical substance used in a chemical
reaction to detect, measure, examine, or
produce other substances.

HATU
HATU
Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium
HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-
triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate)
is a reagent used in peptide coupling chemistry to
generate an active ester from a carboxylic acid. HATU is
used along with Hünig's base (N,N-
diisopropylethylamine, DIPEA), or triethylamine to form
amide bonds. Typically DMF is used as solvent, although
other polar aprotic solvents can also be used.

Reaction Mechanism

 HATU is commonly encountered in amine acylation reactions (i.e., amide
formation). Such reactions are typically performed in two distinct reaction
steps: (1) reaction of a carboxylic acid with HATU to form the OAt-active
ester; then (2) addition of the nucleophile (amine) to the active ester
solution to afford the acylated product.
 The reaction mechanism of carboxylic acid activation by HATU and
subsequent N-acylation is summarised in the figure below. The mechanism
is shown using the more commonly encountered and commercially
available iminium isomer; a similar mechanism, however, is likely to apply
to the uronium form. In the first step, the carboxylate anion (formed by
deprotonation by an organic base [not shown]) attacks HATU to form the
unstable O-acyl(tetramethyl)isouronium salt. The OAt anion rapidly attacks
the isouronium salt, affording the OAt-active ester and liberating a
stoichiometric quantity of tetramethylurea. Addition of a nucleophile, such
as an amine, to the OAt-active ester results in acylation.
 The high coupling efficiencies and fast reaction rates associated with HATU
coupling are thought to arise from a neighbouring group effect brought
about by the pyridine nitrogen atom, which stabilises the incoming amine
through a hydrogen-bonded 7-membered cyclic transition state.

N,N'-Dicyclohexylcarbodiimide
DCC is powerful dehydrating agent.

Properties
Molecular formula C13H22N2
Molar mass 206.33 g mol−1
Appearance white crystalline powder
Density 1.325 g/cm3, solid
Melting point 34 °C, 307 K, 93 °F
Boiling point 122°C (395 K at 6 mmHg)
Solubility in water not soluble

Stored in anhydrous conditions.
Potent skin irritant.
It is waxy low-melting solid.
It is highly soluble in dichloromethane,
tetrahydrofuran, acetonitrile and dimethylformamide,
but insoluble in water.
 The compound is often abbreviated DCC.

Preparations
C6H11NC + C6H11NH2 + O2 → (C6H11N)2C + H2O

p-CH 3 C6H4 SO2 Cl
NH C NH Hot Pyridine
N C N + H2O

Hg 2O
NH C NH + Hg 2S + H2O
N C N
S

Applications
Synthesis of ester
Synthesis of peptide
Synthesis of peroxide
Synthesis of amides
Heterocyclisation reactions
Dehydroxylation of alcohols
Synthesis of α,β-unsaturated ketones and ester
Synthesis of ethers and thioethers
Synthesis of α-diazoketones

Synthesis of ester
C6H11
O
O N H
R C OH
R C
+ H11 C6 N C N C6H11
+ O C
1
R O 1 N H
R O
H C6H11

C6H11
O
O N
R C OH
R C
+ C
O NH
H11 C6 N C N C6H11
C6H11

C6H11
- C6H11
O
-
N O +
P. T . N H
R C
C R C
C
O NH
1 O NH
1 . .+ R O
R .O. C6H11
C6H11
H
C6H11 C6H11
-
O +
N H O N H
R C R C
C + O C
1 O NH 1 NH
R O R O
C6H11 C6H11

Synthesis of peptide

Diisobutylaluminium hydride
DIBAL-H
H3C
CH CH 2
H3C
Al
H3C H
CH CH 2
H3C

H3C CH3
CH CH 2 CH2 HC
H3C H CH3
Al Al
H3C H CH3
CH CH 2 CH 2 HC
H3C CH3
Properties
Molecular formula C16H38Al2 (dimer)
Molar mass 142.22 (monomer)
Appearance colorless liquid
Density 0.798 g/cm3
Melting point –18 °C
Boiling point 116–118 °C/1 mmHg
Solubility in hydrocarbon solvents
Preparation H3C CH3
CH
CH 2
H3C CH3
H3C
Al
3 C CH2 + 3/ 2 H2 + Al CH CH 2 CH 2 HC
H3C CH3
H3C
o
140 C
H3C CH3
H3C Al
CH CH 2 CH 2 HC
C CH2 +
H3C CH3
H3C
Applications
Reduction of Esters and lactones

Reduction on Nitrile

Reduction of esters and lactones
CH3
O CH3 O Al CH 2 HC
R C + H Al CH 2 HC
o
R C H CH3
2
- 78 C
CH3
OR' 2 OR'
Stable Complex
H2O
H3C O H
CH CH 2 Al OH + R C H
H3C 2 OR'
Hemiacetal
R' OH + R C H

H3C
CH 2 H3C
CH CH 2
COOC 2H5
CH CHO
O DIBAL-H
O
o
H2C S CH3 -78 C
H2C S CH3
DIBAL-H
o
25 C
H3C
CH 2
CH CH 2OH
O
H2C S CH3

H3CO H3CO
DIBAL-H
N o
- 60 C N
H3CO H3CO
C2H5 C2H5
CH 2COOC 2H5 H2C CHO

O
O
OH
CH 2
DIBAL-H CH 2 CHO
o
- 78 C
DIBAL-H
O O
CH3 o CH CH3
- 78 C / Toluene
CH3 O CH3 OH
CHO
O

Reduction of Nitriles
CH3
R C N + H Al CH 2 HC
CH3
2
CH3
H2O
R C O
R CH N Al CH 2 HC
H CH3
2

H3C CH CH CH 2 CH 2 CH 2 C N
o
( i ) DIBAL - H / -80 C / Toluene
( ii ) H 2O
H3C CH CH CH 2 CH 2 CH 2 C O

O CH 2 O CH 2
O O
o
( i ) DIBAL - H / - 70 C
+
( ii ) H 2O / H
C N C O
C N o C O
( i ) DIBAL - H / - 70 C
+
( ii ) H 2O / H
CH2 CH2
CH3 CH3

Dithianes
Sulfur atom of thiol is far better nucleophile than the
oxygen atom of an alcohol.
Thiols add to carbonyl group of aldehydes and ketones
in presence of acid catalyst to form 1,3-dithiane.
R +
H
O + CH 2 CH 2
S S
H HS SH C
R H
1, 3 - Dithiane 1, 3 - Dithiane

The carbonyl carbon atom of an aldehyde is positive.
It is electrophile and react with nucleophiles.
When the aldehyde is converted to 1,3-dithiane and

treated with butyllithium, this same carbon becomes
negatively charged and reacts with electrophile.
This reversal of polarity of the carbonyl carbon atom is

called umpolung ( polarity reversal).

That is electrophilic into nucleophilic and
nucleophilic into electrophilic transformation.
BuLi / THF
o
S S - 20 C S S S S
-
C C C
+
R H R Li R Li
1, 3 - Dithiane 2-Lithio- 1, 3 - dithiane

Reaction with Halides
O BuLi / THF
HS - ( CH 2 )3 - SH
o
S S - 20 C S S
C C
R H
R H R Li
R-X
O
HgCl 2 / HOH
S S
R R
C
R R

Reaction with Halides
O BuLi / THF
HS - ( CH 2 )3 - SH
o
S S - 20 C S S
C C
R H
R H R Li
R' - CH 2 - X
HS - ( CH 2 )3 - SH + HgCl 2 / HOH
S S
R CH 2 - R'
C
R CH 2 - R'
O BuLi / THF
HS - ( CH 2 )3 - SH
o
S S - 20 C S S
C C
H H
H H H Li
R - CH 2 - X
HS - ( CH 2 )3 - SH + HgCl 2 / HOH
CH 3OH S S
H CH 2 - R
C
H CH 2 - R
( I ) BuLi / THF
( II ) R' - CH 2 - Br
( III ) HgCl 2 / HOH

CH 3OH
O
R CH 2 C CH 2 R'

CHO CHO S S S S
2 HS - ( CH 2 )3 SH / THF
( I ) BuLi
( II ) Br - ( CH 2 )3 - Cl
( CH 2 )3
O
O
HgCl 2 / HOH / CH 3CN S S S S
( CH 2 )3

Reaction with epoxide
BuLi H2C CH 2 R'
S S S S O
-
C S S
+
R H R Li
R CH 2 CH R'
- +
O Li
+
HgCl 2 / H2O / H
R CH 2 CH R'
OH

Carbonyl compounds
O S O Li
S
- + Ph
C Li + Ph
R R
S Ph S Ph
HgCl 2 / H2O / CH 3CN
O OH
R C C Ph
Ph

Reaction with Nitriles
H2O Heat
S S S S
- S S
C C
+ C
R Li N Li
O
+ R C R C
R'
R' C N R'
HgCl 2 / H2O / CH 3OH
O O
R C C R'
vic dicarbonyl

Reaction with acid chloride
S S
-
S S S S C S S
-
C OH
+ O H
H Li
H H H
+ R R
O S S
R Cl
OH
OHC CHO

Reaction with CO2
S S S S
-
C
+ O
R Li
R
+ O Li
O C O +
H2 O / H

O
S S
O O
R R
O H O H

LDA

LDA is a hindered non-
nucleophilic strong base with which
deprotonation can be achieved
without interference by
nucleophilic attack.
It is very poor nucleophile and

does not give nucleophilic
substitution.
LDA is ideal base for generation of
carbanion or enolate anion from
carbonyl group containing
compounds.

Preparation of silyl enol ethers

Direct alkylation and acylation of ketones

An aldol condensation via the kinetic enolate using LDA

α-selenation : Synthesis of α,β-unsaturated cabonyl
compounds from isolated carbonyl compounds

Alkylation of acids, esters, amides,
imines & nitriles in presence of LDA

Sodium cyanoborohydride
[NaBH3CN]
 Sodium cyanoborohydride is the inorganic compound with
the formula NaBH3(CN). This colourless salt is widely used
in organic synthesis for the reduction of imines.

The reagent may be prepared, either by
treating sodium cyanide with borane.
By reacting sodium borohydride with
mercury(II) cyanide.
Owing to the presence of the electron-

withdrawing cyanide substituent, [B(CN)H3]−
is far less nucleophilic than is [BH4]−, as found
in sodium borohydride.
Sodium cyanoborohydride is a mild reducing agent that
converts imines to amines.

It can be used to exchange the oxygen for an amine group
on the carbonyl carbon of aldehydes or ketones when

reacted with ammonia or a primary amine.
Selectivity is achieved at mildly basic solutions (pH 7-10).
 Owing to this selectivity, the reagent is ideal for reductive
aminations.
This reduction is known sometimes as the Burch Reaction.

The salt is mildly water-sensitive, but tolerates aqueous
conditions.
In addition, sodium cyanoborohydride is often used in
hydrogenolysis reactions, such as the opening of acetals.

Reductive amination (also known as reductive
alkylation) is a form of amination that involves the
conversion of a carbonyl group to an amine via an
intermediate imine. The carbonyl group is most
commonly a ketone or an aldehyde.

 In this organic reaction, the amine first reacts with the
carbonyl group to form a hemiaminal species, which

subsequently loses one molecule of water in a reversible
manner by alkylimino-de-oxo-bisubstitution, to form the
imine.
 The equilibrium between aldehyde/ketone and imine can be
shifted toward imine formation by removal of the formed

water through physical or chemical means. This
intermediate imine can then be isolated and reduced with a
suitable reducing agent (e.g., sodium borohydride). This is
indirect reductive amination.
Properties
Molecular formula NaBH3CN
Molar mass 62.84 g/mol
white to off-white
Appearance
powder, hygroscopic
Density 1.20 g/cm3

Melting point 241 °C decomp.
Solubility in water soluble

Reductive amination
CH3
O
H N
CH3
H3C
NaBH 3CN
NH
+
H3C

Reduction of oxime
N OH HN OH
NaBH 3CN
H3C C CH 2 CH3 H3C CH CH 2 CH3

Reductive Amination of Aldehyde / Ketone
H3C H3C R H3C R
NaBH 3CN
O + HN R 2 N
+
H C N
H3C H3C R H3C R
-
R1 R1 O R1 OH
NaBH 3CN
O + R NH OH +
N H C N
R2 R2 R R2 R

Alkyl hydrazine
CH3
2 HCHO
N NH2 N N
NaBH 3CN
CH3
CHO
H2C NaBH 3CN
N NH2 + N N
H2C
CHO

Dess-Martin periodinane

Preparations of Dess-Martin
Periodinane
Dr. Hitesh D. Patel 12/19/2023 83

Preparation
2-Iodobenzoic acid is oxidized preferably by Oxone, or
by KBrO3 to 2-iodoxybenzoic acid.

(Caution: 2-Iodoxybenzoic acid has been found to be
impact and heat sensitive, decomposing explosively.)

 The 2-Iodoxybenzoic acid is then treated with a
mixture of acetic anhydride, acetic acid and p-

toluenesulfonic acid at 80-100 °C for 40 min. The
resulted solids can be obtained via filtration and
washing with ether.
Properties
Molecular formula C13H13IO8
Molar mass 424.14 g/mol
white powder, chips,

Appearance crystals or crystalline
powder and/or chunks
Density 1.362 g/cm3 solid
Melting point 103 - 133 °C

The Dess-Martin periodinane (DMP) is
commercially available and decomposes only
slowly.
But DMP is heat- and shock-sensitive, and shows
an exotherm when heated >130 °C.

2-Iodoxybenzoic acid (IBX), the impact-sensitive
intermediate in the synthesis of the Dess-Martin

periodinane, is available in a DMSO solution and is
also used as an oxidizing agent.
Uses and advantage of DMP
Dess-Martin periodinane is mainly used as an
oxidant for complex, sensitive and

multifunctional alcohols.
One of the reasons for its effectiveness is its high
selectivity towards complexation of the

hydroxylic group, which allows alcohols to rapidly
perform ligand exchange; the first step in the
oxidation reaction.
Its effectiveness as an oxidant is also due to its
versatility; having a broad scope of being able to

convert alcohols to carbonyl derivatives.
Its reactions and yield are also known to be clean
and high respectively.

Work up is also clean and simple.
By products from the reaction can be removed
easily by precipitation, filtration or

chromatography.
Dess-Martin Oxidation

Mechanism of the Dess-Martin Oxidation

Name Reactions (Dess-Martin-Oxidation )

Alcohols are oxidized to the corresponding
carbonyl compounds

2,3-Dichloro-5,6-dicyano-1, 4-benzoquinone
DDQ

The high potential is a powerful
dehydrogenating agent.
Reaction with DDQ may be carried out in
the inert solvent such as benzene, toluene,

dioxane, THF or acetic acid, but dioxane and
HC solvents are often preferred, because
DDQH2 formed in these solvents is
insoluble and can be removed by filtration.
OH
O
Cl
Cl CN
CN A B
+ + A B
H H
Cl CN
Cl CN
OH
O
DDQ DDQH 2

O OH
Preparation O OH
Cl
CN CN CN
HCN [O] HCl
+
C2H5OH / H
CN CN CN
O OH O OH
[O]
O OH O
Cl Cl Cl
CN [O] CN CN
HCl
Cl CN Cl CN CN
O OH O

Properties
Molecular formula C8Cl2N2O2
Molar mass 227 g mol−1
Melting point 210-215 °C (dec.)

Mechanism of dehydrogenation
H H OH
O
Cl Cl
H CN CN
+
+
CH
+
Cl CN Cl CN
-
O O
DDQ
OH
Cl
CN
+
Cl CN
OH

This oxidant is useful for the
dehydrogenation of alcohols, phenols
and steroid ketones in organic
chemistry.

Stability
DDQ can react with water and give off
hydrogen cyanide (HCN), which is highly

toxic. Storage should be in dry area. Low
temperature and weak acid environment
can increase the stability of DDQ.

Reactions
Benzylic oxidation
DDQ
CH3
CH3 H3CO O
H3CO O DDQ
CH3
CH3
OCH 3
OCH 3

Dehydrogenation

Oxidative Coupling

n-Butyllithium
C4H9Li
Preparation
The standard preparation for n-BuLi is reaction
of 1-bromobutane or 1-chlorobutane with Li

metal:
2 Li + C4H9X → C4H9Li + LiX
where X = Cl, Br
Properties
Molecular formula C4H9Li
Molar mass 64.06 g mol−1
colorless liquid
unstable
Appearance
usually obtained
as soln
Density 0.68 g/cm³, solvent defined
Melting point -76 °C (<273 K)
Boiling point decomposes
Solubility in water reacts violently
Solubility in diethyl ether soluble
Acidity (pKa) >35 (need source)

Applications
Butyllithium is principally valued as an initiator for the
anionic polymerization of dienes, such as butadiene.

The reaction is called "carbolithiation":
C4H9Li + CH2=CH-CH=CH2 → C4H9-CH2-CH=CH-CH2Li
Isoprene can be polymerized stereospecifically in this
way. Also of commercially importance is the use of

butyllithium for the production of styrene-butadiene
polymers. Even ethylene will insert into BuLi.

n-Butyllithium (abbreviated n-BuLi) is an
organolithium reagent. It is widely used as a

polymerization initiator in the production of
elastomers such as polybutadiene or styrene-
butadiene-styrene (SBS). Also, it is broadly
employed as a strong base (superbase) in
organic synthesis, both industrially and in the
laboratory.
Reactions
Butyllithium is a strong base (pKa ≈ 40), but it is also a
powerful nucleophile and reductant, depending on the

other reactants. Furthermore, in addition to being a strong
nucleophile, n-BuLi binds to aprotic Lewis bases, such as
ethers and tertiary amines, which partially disaggregate
the clusters by binding to the lithium centers. Its use as a
strong base is referred to as metalation. Reactions are
typically conducted in tetrahydrofuran and diethyl ether,
which are good solvents for the resulting organolithium
derivatives.
Halogen-lithium exchange
Butyllithium reacts with some organic bromides
and iodides in an exchange reaction to form the

corresponding organolithium derivative. The
reaction usually fails with organic chlorides and
fluorides:
C4H9Li + RX → C4H9X + RLi (X = Br, I)
(R+ & X-) (R- & Li+)
2 C4H9Li + R'CH=CHBr → 2 C4H10 + R'C≡CLi + LiBr

Transmetalations
A related family of reactions are the

transmetalations, wherein two organometallic
compounds exchange their metals. Many
examples of such reactions involve Li exchange
with Sn:
C4H9Li + Me3SnAr → C4H9SnMe3 + LiAr

Carbonyl additions
Organolithium reagents, including n-BuLi are used in
synthesis of specific aldehydes and ketones. One such

synthetic pathway is the reaction of an organolithium
reagent with disubstituted amides:
R1Li + R2CONMe2 → LiNMe2 + R2COR1

Degradation of THF
 THF is deprotonated by butyllithium, especially in the
presence of TMEDA, by loss of one of four protons adjacent

to oxygen. This process, which consumes butyllithium to
generate butane, induces a reverse cycloaddition to give
enolate of acetaldehyde and ethylene.
 Therefore, reactions of BuLi in THF are typically
conducted at low temperatures, such as –78 °C, as is
conveniently produced by a freezing bath of dry
ice/acetone. Higher temperatures (-25 °C or even -15 °C) are
also used.
Thermal decomposition
When heated, n-BuLi, analogously to other
alkyllithium reagents with "β-hydrogens",

undergoes β-hydride elimination to produce 1-
butene and LiH:
C4H9Li → LiH + CH3CH2CH=CH2

Safety
Alkyl-lithium compounds are stored under inert
gas to prevent loss of activity and for reasons of

safety. n-BuLi reacts violently with water:
C4H9Li + H2O → C4H10 + LiOH
BuLi also reacts with CO2 to give lithium

pentanoate:
C4H9Li + CO2 → C4H9CO2Li
Phase Transfer Catalysis
 Phase-Transfer Catalysis, "PTC," technology is used in the
commercial manufacture of more than $10 billion per year of

chemicals.
 Monomers Additives
 Surfactants Polymers
 Flavors & Fragrances Petrochemicals
 Agricultural Chemicals Dyes
 Rubber Pharmaceuticals
 Explosives Fine organic chemicals

Desired Reaction
 O-Alkylation (Etherification) N-Alkylation
 C-Alkylation & Chiral Alkylation S-Alkylation
 Dehydrohalogenation Esterification
 Other Nucleophilic Aliphatic &
Aromatic Substitution
 Oxidation Epoxidation & Chiral
Epoxidation
 Michael Addition Aldol Condensation
 Wittig Darzens Condensation
 Carbene Reactions Thiophosphorylation
 Reduction Carbonylation
 HCl/HBr Reactions Transition Metal Co-Catalysis
 Displacement With Cyanide Hydroxide, Hydrolysis Fluoride
Thiocyanate, Cyanate Iodide Sulfide, Sulfite Azide Nitrite, Nitrate
 Any Reaction Above for Polymerization
 Any Reaction Above for Modifying Polymers
What is Phase-Transfer Catalysis?
Phase-Transfer Catalysis is useful primarily for
performing reaction between anions and organic

substrates.
PTC is needed because many anions (in the form
of their salts, such as NaCN) and neutral

compounds are soluble in water and not in
organic solvents, whereas the organic reactants
are not usually soluble in water.
The name phase-transfer catalysis does what it
says...the catalyst acts as a shuttling agent by

extracting the anion or neutral compound from
the aqueous (or solid) phase into the organic
reaction phase (or interfacial region) where the
anion or neutral compound can freely react with
the organic reactant already located in the
organic phase.

Since the catalyst is often a quaternary ammonium
salt (e.g., tetrabutyl ammonium, [C4H9]4N+), also called
the "quat" and symbolized by Q+, the ion pair Q+X- (X-
being the anion to be reacted) is a much looser ion
pair than say Na+X-. This looseness of the ion pair is a
third key reason for enhanced reactivity, which will
ultimately lead to increased productivity (reduced
cycle time) in commercial processes. At the end of the
reaction, an anionic leaving group is usually
generated.

This anionic leaving group is conveniently brought
to the aqueous (or solid) phase by the shuttling
catalyst, thus facilitating the separation of the
waste material from the product. This mechanism
is called the "extraction mechanism" of phase-
transfer catalysis and is shown in Figure

High Yield Solvent-Free Hazardous Nucleophilic
Displacement

Thiolation (Methyl Mercaptan)
Etherification (O-Alkylation)11

Selected Applications and Impressive Performance
Outstanding Reduction of Excess Hazardous
High Volume Raw Material

Oxidation (Hypochlorite)

Oxidation (Air)
Oxidation (H2O2)

Epoxidation & Chiral Epoxidation
Cyanation

Conclusion
Phase-Transfer Catalysis delivers high productivity,
enhanced environmental performance, improved
safety, better quality and decreased plant operability
in hundreds of commercial manufacturing processes
for organic chemicals in dozens of reaction categories.
Companies can achieve higher performance using PTC by
developing these processes and manufacturing in-house or
by outsourcing the development and/or manufacture using
PTC. Most companies are not even aware that they can
gain short term benefit to long term benefit using
PTC. As a result, much opportunity is being missed.
Strategic alliances exist specifically for helping companies
enhance performance by identifying, evaluating and
commercializing opportunities using PTC.

Reagents 2021 LETEST

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Reagents 2021 LETEST

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Reagents in Organic Synthesis

12/19/2023 Dr. Hitesh D. Patel 1

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• (1) A chemical species of particular interest,

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Molar mass 206.33 g mol−1

Appearance white crystalline powder

Density 1.325 g/cm3, solid

Melting point 34 °C, 307 K, 93 °F

Boiling point 122°C (395 K at 6 mmHg)

Solubility in water not soluble

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C6H11NC + C6H11NH2 + O2 → (C6H11N)2C + H2O

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Reduction of Esters and lactones

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CH 2COOC 2H5 H2C CHO

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It is electrophile and react with nucleophiles.

When the aldehyde is converted to 1,3-dithiane and

This reversal of polarity of the carbonyl carbon atom is

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1, 3 - Dithiane 2-Lithio- 1, 3 - dithiane

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1, 3 - Dithiane 2-Lithio- 1, 3 - dithiane

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1, 3 - Dithiane 2-Lithio- 1, 3 - dithiane

1, 3 - Dithiane 2-Lithio- 1, 3 - dithiane

( III ) HgCl 2 / HOH

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HgCl 2 / H2O / CH 3CN

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HgCl 2 / H2O / CH 3OH

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HgCl 2 / H2O / CH 3CN

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HgCl 2 / H2O / CH 3CN

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