Grignard reagents are compounds of the general formula R-Mg-X, where:

• R is an organic group (like alkyl, aryl).

• X is a halogen (like Cl, Br, or I).

How are they used?

Grignard reagents are super reactive and act as nucleophiles, meaning they
like to attack positively charged or electron-de cient areas in other molecules.

What can they do?

1.Add to carbonyl compounds (like aldehydes, ketones, and esters):
• With aldehydes: They create secondary alcohols.
• With ketones: They create tertiary alcohols.
• With esters: They can create tertiary alcohols after two
additions.
2.React with carbon dioxide to make carboxylic acids.
3.Form carbon-carbon bonds, which is critical in building bigger organic
molecules.

Example reaction:
Let’s say we have CH3MgBr (methyl magnesium bromide) and we react it
with formaldehyde (HCHO).
The product will be ethanol (CH3CH2OH) after adding water.
How do you think Grignard reagents might be useful for synthesizing complex
molecules?
Great! Let’s start with oxidation reagents, as they’re frequently tested and
fundamental to organic synthesis. I’ll explain a few important ones step by
step.

1. Jones Reagent (CrO₃ in H₂SO₄ and acetone)

• Purpose: Oxidizes primary alcohols to carboxylic acids and secondary
alcohols to ketones.
• Mechanism: The alcohol reacts with chromium species to form a
chromate ester, which then decomposes to the oxidized product.
• Example:
• Ethanol (CH₃CH₂OH) oxidized by Jones reagent becomes acetic
acid (CH₃COOH).
• Key feature: Doesn’t stop at aldehyde for primary alcohols—goes all
the way to a carboxylic acid.
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Question for you: How would propan-2-ol react with Jones reagent? What
product would form?

2. PCC (Pyridinium Chlorochromate)

• Purpose: Mild oxidizing agent that converts primary alcohols to
aldehydes and secondary alcohols to ketones.
• Key difference from Jones reagent: Stops at the aldehyde stage for
primary alcohols.
• Example:
• Ethanol oxidized by PCC gives acetaldehyde (CH₃CHO).

Question for you: What would happen if you used PCC on cyclohexanol?

3. KMnO₄ (Potassium Permanganate)

• Purpose: A strong oxidizer that converts:
• Primary alcohols to carboxylic acids.
• Secondary alcohols to ketones.
• Alkenes to diols or carboxylic acids (depending on conditions).
• Example:
• Oxidation of cyclohexene with KMnO₄ under acidic conditions
yields adipic acid.

Challenge for you: If KMnO₄ reacts with ethene under basic conditions, what
product forms?

Adam’s Reagent
Adam’s reagent is platinum dioxide (PtO₂), commonly used as a catalyst
in organic chemistry for hydrogenation reactions. It was named after the
chemist Roger Adams, who developed its use. Let’s break it down!

What does it do?

Adam’s reagent facilitates the addition of hydrogen (H₂) to unsaturated
organic compounds like:
1.Alkenes Converts to alkanes.
2.Alkynes Converts to alkanes (if the reaction goes to completion).
3.Nitro compounds Converts to amines.
4.Ketones and aldehydes Converts to alcohols.

How does it work?

 1.Catalyst preparation: Adam’s reagent is used with molecular hydrogen
(H₂ gas). It acts as a surface where the H₂ is activated (split into hydrogen
atoms).
2.Reaction mechanism:
• The organic compound adsorbs onto the surface of the platinum
catalyst.
• Activated hydrogen atoms add step-by-step to the double or triple
bonds in the molecule, resulting in hydrogenation.

Example Reaction:
Hydrogenation of ethene (CH₂=CH₂):
Ethene reacts with Adam’s reagent and H₂ to produce ethane (CH₃-CH₃).

Special features:
• Adam’s reagent is highly selective and ef cient.
• Works under mild conditions.
• Often used in the hydrogenation of sensitive molecules without over-
reduction.

Question for you:

If you treat cyclohexene (C₆H₁₀) with Adam’s reagent and hydrogen gas, what
product do you expect?

Great question! When multiple types of compounds are present, Adam’s

reagent (PtO₂) with hydrogen gas prioritizes reactions based on the reactivity
of the functional groups. Here’s the order of preference in general:

1. Compounds with Double or Triple Bonds

• Adam’s reagent will rst hydrogenate alkenes and alkynes, as these
are the most reactive.
Example: If you have both an alkene and a nitro group, the alkene will be
hydrogenated rst.

2. Nitro Groups (–NO₂)

• After double/triple bonds, it targets nitro groups to reduce them to
amines (R–NH₂).

3. Ketones and Aldehydes

• If alkenes or alkynes are absent, it will reduce ketones and aldehydes
to their corresponding alcohols.
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 4. Aromatic Compounds (Under Harsh Conditions)
• Hydrogenation of aromatic rings (like benzene to cyclohexane) happens
last because aromatic systems are stabilized by resonance and require
more energy to hydrogenate.

Key Factors Affecting Priority:

1.Reactivity: Alkenes and alkynes are the most reactive because their π-
bonds are easy to break.
2.Steric hindrance: Less crowded molecules react more easily.
3.Reaction conditions: Under mild conditions, hydrogenation may stop
at speci c intermediates, while harsh conditions can reduce less reactive
groups (e.g., aromatic systems).
Challenge Question:
If a molecule contains both an alkene and a ketone, and it reacts with Adam’s
reagent under standard conditions, which group will be reduced rst? Why?
You’re on the right track! Yes, Adam’s reagent typically prioritizes double
bonds (like alkenes or allenes) because π-bonds in alkenes are more
reactive and easier to break compared to nitro groups or carbonyl
compounds. Let’s con rm your reasoning step by step:

1. Double Bonds (Alkenes/Allenes)

• Reason for priority: The π-bonds in alkenes/allenes are less stable
and easier to break during hydrogenation, compared to the bonds in nitro or
carbonyl groups.
• In your example, the double bond will reduce rst to form a single bond.

2. Nitro Groups
• These are reduced to amines after alkenes because breaking the N=O
bonds requires more energy compared to π-bonds in alkenes.
• Hydrogenation of nitro groups: Requires stronger reducing
conditions than alkenes.

3. Other Groups (Carbonyl, Aromatic, etc.)

• Groups like ketones, aldehydes, and aromatic systems react only after
all simpler unsaturated systems (like double bonds) are saturated.

Correct Understanding:
You are correct that alkenes/allens will react rst due to their reactive π-
bonds.
Do you want to try a new example, or shall we explore another reagent?
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Alright! Let’s dive into another important reagent: Lithium Aluminium
Hydride (LiAlH₄).

Lithium Aluminium Hydride (LiAlH₄)

• Purpose: LiAlH₄ is a powerful reducing agent used to reduce a variety
of compounds.
• Reaction Medium: It reacts in aprotic solvents like ether, and the
reaction is typically quenched with water or an acid (H₂O or H⁺).

What does it reduce?

LiAlH₄ reduces the following groups, often all the way to their most reduced
forms:
1.Aldehydes and Ketones Alcohols
2.Esters and Carboxylic Acids Primary Alcohols
3.Amides Amines
4.Nitriles Amines
5.Epoxides Alcohols

How does it work?

LiAlH₄ supplies hydride ions (H⁻) that attack the electrophilic carbon in polar
bonds (e.g., C=O, C≡N). This leads to the cleavage of these bonds and
formation of reduced products.

Example Reaction:
1.Reduction of a Ketone:
Acetone (CH₃COCH₃) + LiAlH₄ Isopropanol (CH₃CH(OH)CH₃)
2.Reduction of an Ester:
Ethyl acetate (CH₃COOCH₂CH₃) + LiAlH₄ Ethanol (CH₃CH₂OH) + Methanol
(CH₃OH)

Special Features:
• Very strong reducing agent—it will reduce esters and carboxylic acids,
which weaker agents like NaBH₄ cannot.
• Not selective—reduces multiple groups in one molecule if they’re
present.
Challenge Question:
If a compound contains both an aldehyde and an ester group, and you use
LiAlH₄, which group will be reduced rst? Why?
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You’re absolutely right about LiAlH₄ reducing both groups because it’s a non-
selective reducing agent. However, let’s re ne the reasoning a bit:

Correct Answer: Aldehyde reduces rst.

Why?
1.Reactivity of Aldehydes vs. Esters:
• Aldehydes are more reactive than esters because the carbonyl
carbon in aldehydes is less stabilized (it lacks resonance stabilization or
electron donation from additional groups like in esters).
• In esters, the lone pair on the oxygen of the alkoxy group partially
stabilizes the carbonyl carbon, making it slightly less electrophilic than
aldehydes.

How LiAlH₄ Reacts:

• LiAlH₄ will attack the most electrophilic carbon rst. Since the carbon
in an aldehyde is more electrophilic than in an ester, the aldehyde gets
reduced faster.

Overall Result:
LiAlH₄ reduces both groups in the end, but the aldehyde reacts rst, followed
by the ester.
Test Yourself: If you have a molecule with a ketone and a carboxylic acid,
which group will LiAlH₄ reduce rst? Why?

Exactly! You nailed it—ketones are reduced rst by LiAlH₄ because:

1.Ketones are less stabilized compared to carboxylic acids.
• Carboxylic acids have resonance between the carbonyl group and
the hydroxyl group, which reduces the electrophilicity of the carbonyl
carbon.
• In contrast, ketones lack this resonance stabilization, making their
carbonyl carbon more reactive and prone to attack by a hydride ion (H⁻)
from LiAlH₄.
2.Electrophilicity matters: Ketones have a more electrophilic carbonyl
carbon than carboxylic acids, so LiAlH₄ attacks them rst.

Final Reaction Order:

1.Ketones are reduced to secondary alcohols.
2.Carboxylic acids are reduced to primary alcohols later, as this requires
more energy due to the stabilized structure.
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Challenge Question:
If you have a molecule with a ketone, an ester, and an alkene, which group
will LiAlH₄ reduce rst?

Exactly! You’re absolutely right—ketone will be reduced rst in this case, and
here’s why:

1. Why ketone rst?

• Among ketone, ester, and alkene, the ketone has the most electrophilic
carbon because it lacks the resonance stabilization of the ester group.
• This makes the ketone carbonyl more reactive and attacked rst by the
hydride ion from LiAlH₄.

2. What about the ester?

• The ester will also be reduced eventually, but after the ketone because
its carbonyl is less electrophilic due to resonance from the -OR group.

3. Can LiAlH₄ reduce alkenes?

• No, you’re correct that LiAlH₄ cannot reduce alkenes. It’s selective for
polar bonds like C=O, C≡N, or C=O in esters, but it doesn’t affect the non-
polar π-bonds in alkenes.

Final Reaction Order:

1.Ketone Reduced to a secondary alcohol.
2.Ester Reduced to a primary alcohol.
3.Alkene Remains unchanged.

Challenge Question:
If you have a molecule with a nitrile (C≡N) and a ketone, which group will
LiAlH₄ reduce rst? Why?

You’re close in your reasoning, but let’s clarify! While the cyano group (C≡N)
is indeed highly polar, the ketone will still be reduced rst by LiAlH₄. Here’s
why:

Key Reason: Ketone is more reactive than C≡N

1.Electrophilicity of Carbon:
• The carbon in the ketone’s carbonyl group (C=O) is more
electrophilic than the carbon in the cyano group (C≡N) due to the
electronegativity of the oxygen and the lack of strong resonance
stabilization.
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 • In the cyano group, the carbon is stabilized by resonance with
nitrogen, which makes it less reactive compared to the ketone.
2.Mechanism Preference:
• LiAlH₄ attacks C=O bonds more readily than the C≡N bond
because breaking the π-bond of the carbonyl group is easier than
breaking the triple bond of the nitrile.

Order of Reduction:
1.Ketone Reduced to a secondary alcohol rst.
2.C≡N Reduced to a primary amine (R–CH₂–NH₂) after the ketone.

Final Thought:
While the cyano group is highly polar, its carbon is less electrophilic
compared to the ketone due to resonance stabilization. That’s why the ketone
is reduced rst.
Challenge Question: If a molecule contains both a carboxylic acid and a
nitrile group, which group will LiAlH₄ reduce rst? Why?
Correct! The nitrile group (C≡N) will be reduced rst over the carboxylic
acid, and here’s why:

1. Nitrile Reduction is Easier

• In nitriles, the carbon atom is highly polarized due to the
electronegativity of nitrogen, making it a good electrophilic target for LiAlH₄.
• Carboxylic acids are more stabilized by resonance and hydrogen
bonding, which makes their reduction slower and requires more energy.

2. Mechanism Matters
• The hydride ion (H⁻) from LiAlH₄ attacks the C≡N group more readily,
reducing it to a primary amine (R–CH₂–NH₂).
• The reduction of the carboxylic acid to a primary alcohol happens only
after the nitrile is reduced.

Order of Reduction:
1.Nitrile (C≡N) Reduced to a primary amine (R–CH₂–NH₂).
2.Carboxylic Acid (COOH) Reduced to a primary alcohol (R–
CH₂OH).

Challenge for You:

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 If a molecule contains an ester, a nitrile, and a ketone, which group will LiAlH₄
reduce rst? Why?

Of course! Let’s keep going with some important reagents that are often
asked in exams like CSIR NET. I’ll explain their purpose, mechanism, and
common reactions.

1. NaBH₄ (Sodium Borohydride)

• Purpose: A mild reducing agent that reduces:
• Aldehydes to primary alcohols.
• Ketones to secondary alcohols.
• Key Feature: Cannot reduce esters, carboxylic acids, or nitriles (unlike
LiAlH₄).
• Reaction Example:
• Acetone (CH₃COCH₃) + NaBH₄ Isopropanol (CH₃CH(OH)CH₃).

Challenge for you: If you use NaBH₄ on an ester, what will happen?

2. OsO₄ (Osmium Tetroxide)

• Purpose: Used for syn-dihydroxylation of alkenes (adding two -OH
groups on the same side of a double bond).
• Reaction Example:
• Cyclohexene + OsO₄ cis-1,2-cyclohexanediol.

Question for you: If you use OsO₄ on ethene (CH₂=CH₂), what product will
you get?

3. FeCl₃ (Ferric Chloride)

• Purpose: Works as a Lewis acid catalyst, commonly used in:
• Friedel-Crafts Acylation/Alkylation to generate carbocations.
• Aromatic substitution reactions with electron-rich aromatic rings
(e.g., phenols).

Reaction Example:
Phenol + FeCl₃ Quinonoid-like complex (purple color in phenol detection
test).

Question for you: What happens if FeCl₃ is used with benzene and acetyl
chloride (CH₃COCl)?

4. PCl₅ (Phosphorus Pentachloride)

• Purpose: Converts:
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 • Alcohols to alkyl chlorides.
• Carboxylic acids to acid chlorides.
• Can also chlorinate ketones and aldehydes.

Reaction Example:
Ethanol (CH₃CH₂OH) + PCl₅ Ethyl chloride (CH₃CH₂Cl) + HCl + POCl₃.

Challenge for you: If PCl₅ reacts with acetic acid, what will be the product?

5. Grubbs Catalyst
• Purpose: A catalyst for alkene metathesis (exchange of alkene
groups).
• Reaction Example:
Propene + Ethene New alkenes (e.g., butene and ethylene).

Question for you: What happens when two molecules of ethene react with
Grubbs catalyst?
Which reagent would you like to focus on rst? Or do you want me to keep
listing more?

Absolutely! Let’s dive deeper into some important reagents with detailed
explanations, examples, and mechanisms—just like yesterday. These
reagents are vital for the CSIR NET and understanding organic synthesis.

1. DIBAL-H (Diisobutylaluminium Hydride)

• Purpose: A selective reducing agent for:
• Reducing esters to aldehydes (stopping at aldehyde stage).
• Reducing nitriles (C≡N) to aldehydes.
• Reaction Medium: Works in non-protic solvents like toluene or
hexane at low temperatures (e.g., −78 °C).

Reaction Example 1: Reduction of Ester to Aldehyde

Methyl acetate (CH₃COOCH₃) + DIBAL-H Acetaldehyde (CH₃CHO).

Reaction Example 2: Reduction of Nitrile to Aldehyde

Acetonitrile (CH₃C≡N) + DIBAL-H Acetaldehyde (CH₃CHO).

Key Features:
• Unlike LiAlH₄, DIBAL-H stops at the aldehyde stage for esters and
nitriles.
• Reduces ketones and aldehydes to alcohols, like other hydride donors.
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2. mCPBA (meta-Chloroperoxybenzoic Acid)
• Purpose: A strong oxidizing agent for:
• Epoxidation of alkenes (adds an oxygen atom to form an
epoxide).
• Oxidation of sul des to sulfoxides or sulfones.
• Reaction Medium: Nonpolar solvents like CH₂Cl₂ (dichloromethane).

Reaction Example: Epoxidation of Alkenes

Cyclohexene + mCPBA Cyclohexene oxide (epoxide).

Mechanism:
1.The alkene π-bond attacks the peroxide oxygen.
2.A cyclic transition state forms, leading to the epoxide.

Key Features:
• Stereospeci c: If the starting alkene is cis, the epoxide remains cis.

Challenge: What happens if you use mCPBA on trans-2-butene?

3. NBS (N-Bromosuccinimide)
• Purpose: A mild brominating agent for:
• Allylic and benzylic bromination.
• Formation of bromohydrins from alkenes (with water).

Reaction Example 1: Allylic Bromination

Propene + NBS + Light Allyl bromide (CH₂=CH–CH₂Br).

Reaction Example 2: Bromohydrin Formation

Cyclohexene + NBS + H₂O Bromohydrin (BrCH₂–CHOH–CH₂).

Mechanism:
1.Forms a bromonium ion intermediate.
2.Water or radical substitution completes the reaction.

Challenge: How would NBS react with toluene?

4. SOCl₂ (Thionyl Chloride)

• Purpose: Converts:
• Alcohols to alkyl chlorides.
• Carboxylic acids to acid chlorides.
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 Reaction Example 1: Alcohol to Alkyl Chloride
Ethanol (CH₃CH₂OH) + SOCl₂ Ethyl chloride (CH₃CH₂Cl) + SO₂ + HCl.

Reaction Example 2: Carboxylic Acid to Acid Chloride

Acetic acid (CH₃COOH) + SOCl₂ Acetyl chloride (CH₃COCl) + SO₂ + HCl.

Mechanism:
1.SOCl₂ reacts with the hydroxyl group to form an intermediate.
2.Chloride ion (Cl⁻) displaces leaving groups to give the nal product.

Key Features:
• The reaction produces gaseous byproducts (SO₂ and HCl) for easy
puri cation.

5. LDA (Lithium Diisopropylamide)

• Purpose: A strong, non-nucleophilic base used for deprotonation to
form enolates.
• Key Reaction: Deprotonates α-hydrogens of ketones, esters, or
nitriles.

Reaction Example: Enolate Formation

Acetone + LDA Enolate ion (CH₂⁻=C(OH)CH₃).

Mechanism:
1.LDA abstracts an acidic proton.
2.The enolate ion forms as a resonance-stabilized species.

Challenge: What would happen if LDA reacts with ethyl acetate?

6. Tollen’s Reagent ([Ag(NH₃)₂]⁺)

• Purpose: A mild oxidizing agent used to:
• Oxidize aldehydes to carboxylic acids.
• Identify aldehydes in a silver mirror test.

Reaction Example: Oxidation of Aldehydes

Formaldehyde (HCHO) + Tollen’s reagent Formic acid (HCOOH) + Silver
mirror (Ag⁰).

Mechanism:
1.Aldehyde reduces Ag⁺ ions to metallic silver (Ag⁰).
2.The aldehyde itself is oxidized to a carboxylic acid.
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Key Feature: Does not react with ketones.
Which reagent do you want to focus on? Or should I keep adding more?

Sure! Here are more key reagents often encountered in exams like the CSIR
NET, along with detailed explanations of their uses and reactions:

7. NaNH₂ (Sodium Amide)

• Purpose: A strong base and nucleophile used for:
• Deprotonation of terminal alkynes to form alkynide ions.
• Elimination reactions (e.g., to form alkynes from vicinal dihalides).

Reaction Example 1: Formation of Alkynide Ion

Terminal alkyne (e.g., ethyne) + NaNH₂ Alkynide ion (HC≡C⁻ Na⁺) + NH₃.

Reaction Example 2: Double Elimination to Form Alkynes

1,2-Dibromoethane + 2NaNH₂ Ethyne (HC≡CH) + 2NaBr + NH₃.

Mechanism:
1.NaNH₂ abstracts a proton (H⁺).
2.Successive eliminations form the alkyne.

Challenge: How would NaNH₂ react with 1-bromo-2-chloropropane?

8. Pd/C + H₂ (Palladium on Carbon with Hydrogen)

• Purpose: A catalyst for:
• Hydrogenation of alkenes, alkynes, and other unsaturated
compounds.
• Reduction of nitro groups to amines.

Reaction Example 1: Hydrogenation of Alkenes

Cyclohexene + H₂ + Pd/C Cyclohexane.

Reaction Example 2: Reduction of Nitro Compounds

Nitrobenzene + H₂ + Pd/C Aniline (C₆H₅NH₂).

Key Features:
• Works under mild conditions.
• Selectively reduces π-bonds in alkenes/alkynes rst.

Challenge: What happens when phenylacetylene reacts with Pd/C + H₂?

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9. BF₃·Et₂O (Boron Tri uoride Etherate)
• Purpose: A Lewis acid that:
• Activates carbonyl groups for nucleophilic attack.
• Catalyzes Friedel-Crafts alkylation and acylation.

Reaction Example: Friedel-Crafts Acylation

Benzene + Acetyl chloride (CH₃COCl) + BF₃ Acetophenone (C₆H₅COCH₃).

Key Features:
• Strong electrophile generator.
• Often used in Diels-Alder reactions to activate dienophiles.

Challenge: How would BF₃·Et₂O affect the reactivity of ethyl acetate?

10. KMnO₄ (Potassium Permanganate)

• Purpose: A strong oxidizing agent that oxidizes:
• Alkenes to diols or carboxylic acids.
• Alcohols to carboxylic acids.

Reaction Example 1: Oxidation of Alkenes

Ethene (CH₂=CH₂) + KMnO₄ (cold, dilute) Ethane-1,2-diol (CH₂OH–
CH₂OH).

Reaction Example 2: Oxidation of Alcohols

Ethanol + KMnO₄ Acetic acid (CH₃COOH).

Key Features:
• Alkenes: Cold, dilute KMnO₄ gives diols; Hot, concentrated KMnO₄
cleaves double bonds to carboxylic acids.

Challenge: What product forms when cyclohexene reacts with hot,

concentrated KMnO₄?

11. Zn(Hg), HCl (Clemmensen Reduction)

• Purpose: Reduces ketones and aldehydes to alkanes.
• Reaction Medium: Acidic conditions.

Reaction Example:
Acetophenone (C₆H₅COCH₃) + Zn(Hg), HCl Ethylbenzene (C₆H₅CH₂CH₃).

Mechanism:
1.The ketone/aldehyde reacts with zinc and acid to form a hydrocarbon.
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Key Features:
• Only works in acidic conditions.
• Used for compounds stable under acidic conditions.

Challenge: Can Zn(Hg), HCl reduce carboxylic acids? Why or why not?

12. NaBH(OAc)₃ (Sodium Triacetoxyborohydride)

• Purpose: A mild reducing agent used for:
• Reductive amination: Reduces imines (C=NH) to amines (C–
NH₂).
• Selective reduction of aldehydes in the presence of ketones.

Reaction Example:
Benzaldehyde + Ammonia + NaBH(OAc)₃ Benzylamine (C₆H₅CH₂NH₂).

Key Features:
• Works in protic solvents like methanol or ethanol.
• Doesn’t reduce ketones unless strongly activated.

Challenge: What happens when NaBH(OAc)₃ is used with a ketone and

ammonia?

13. PBr₃ (Phosphorus Tribromide)

• Purpose: Converts:
• Alcohols to alkyl bromides.
• Carboxylic acids to acid bromides.

Reaction Example 1: Alcohol to Alkyl Bromide

Methanol (CH₃OH) + PBr₃ Methyl bromide (CH₃Br).

Reaction Example 2: Acid to Acid Bromide

Acetic acid + PBr₃ Acetyl bromide (CH₃COBr).

Mechanism:
1.PBr₃ reacts with the alcohol, forming a reactive intermediate.
2.Bromide ion displaces the leaving group to form the alkyl bromide.

Key Features:
• Byproducts (like H₃PO₃) are easy to remove.

Challenge: What will be the product when ethanol reacts with PBr₃?
Which of these reagents would you like to explore further? Or should I keep
adding more?

You’re absolutely right! I’ll make sure to clearly mention what types of
molecules each reagent reacts with moving forward, so there’s no
confusion. Let me revise and provide more examples with proper speci city.
Here we go:

14. NaBH₄ (Sodium Borohydride)

• Reacts with:
• Aldehydes Reduced to primary alcohols.
• Ketones Reduced to secondary alcohols.
• Does NOT reduce esters, carboxylic acids, or alkenes.

Example Reaction:
Acetone (CH₃COCH₃) + NaBH₄ Isopropanol (CH₃CH(OH)CH₃).

Key Notes:
• Works on simple carbonyl groups (C=O) only.
• Mild reagent suitable for selective reductions.

15. DIBAL-H (Diisobutylaluminium Hydride)

• Reacts with:
• Esters Reduced to aldehydes at low temperatures (e.g., −78
°C).
• Nitriles (C≡N) Reduced to aldehydes.
• Aldehydes and Ketones Reduced to alcohols.

Example Reaction:
Methyl benzoate (C₆H₅COOCH₃) + DIBAL-H Benzaldehyde (C₆H₅CHO).

Key Notes:
• Works best in non-protic solvents like toluene.
• Does not fully reduce esters/nitriles like LiAlH₄ does.

16. KMnO₄ (Potassium Permanganate)

• Reacts with:
• Alkenes: Oxidized to diols (cold, dilute) or carboxylic acids (hot,
concentrated).
• Primary alcohols: Oxidized to carboxylic acids.
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 • Secondary alcohols: Oxidized to ketones.

Example Reaction:
Cyclohexene (C₆H₁₀) + KMnO₄ (hot, concentrated) Adipic acid (HOOC–
(CH₂)₄–COOH).

Key Notes:
• Doesn’t react with alkynes or tertiary alcohols.

17. OsO₄ (Osmium Tetroxide)

• Reacts with:
• Alkenes Forms cis-diols via syn-dihydroxylation.
• Does NOT react with alkynes, aromatic rings, or saturated
compounds.

Example Reaction:
Cyclohexene (C₆H₁₀) + OsO₄ cis-1,2-cyclohexanediol.

Key Notes:
• Highly speci c for alkenes.
• Often used with co-oxidants like NMO (N-methylmorpholine oxide).

18. SOCl₂ (Thionyl Chloride)

• Reacts with:
• Alcohols Converts to alkyl chlorides.
• Carboxylic acids Converts to acid chlorides.

Example Reaction:
Ethanol (CH₃CH₂OH) + SOCl₂ Ethyl chloride (CH₃CH₂Cl) + SO₂ + HCl.

Key Notes:
• Does not react with ketones, esters, or alkenes.
• Useful for preparing acid chlorides for further synthesis.

19. Tollen’s Reagent ([Ag(NH₃)₂]⁺)

• Reacts with:
• Aldehydes Oxidized to carboxylic acids.
• Does NOT react with ketones, alcohols, or alkenes.

Example Reaction:
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Formaldehyde (HCHO) + Tollen’s Reagent Formic acid (HCOOH) + Silver
Mirror (Ag⁰).

Key Notes:
• Speci c to aldehydes, making it useful as a test for them.

20. NBS (N-Bromosuccinimide)

• Reacts with:
• Alkenes: Forms allylic bromides or bromohydrins.
• Benzylic positions: Forms benzyl bromides.

Example Reaction:
Propene (CH₃CH=CH₂) + NBS + hv Allyl bromide (CH₂=CH–CH₂Br).

Key Notes:
• Speci c for allylic or benzylic hydrogens; doesn’t react with saturated
hydrocarbons.

21. Zn(Hg), HCl (Clemmensen Reduction)

• Reacts with:
• Ketones and Aldehydes: Reduced to alkanes.
• Does NOT reduce carboxylic acids, esters, or nitriles.

Example Reaction:
Acetophenone (C₆H₅COCH₃) + Zn(Hg), HCl Ethylbenzene (C₆H₅CH₂CH₃).

Key Notes:
• Works under acidic conditions; avoids base-sensitive groups.

22. PBr₃ (Phosphorus Tribromide)

• Reacts with:
• Alcohols: Converts to alkyl bromides.
• Carboxylic acids: Converts to acid bromides.

Example Reaction:
Methanol (CH₃OH) + PBr₃ Methyl bromide (CH₃Br).

Key Notes:
• Doesn’t affect alkenes, ketones, or aromatic systems.
Got it! Let’s keep building your reagent library with more detailed entries.
Here are some additional reagents:
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23. NaNO₂ + HCl (Nitrous Acid)
• Reacts with:
• Aromatic amines (R–NH₂): Forms diazonium salts (Ar–N₂⁺Cl⁻) at
low temperatures.
• Primary aliphatic amines: Forms unstable diazonium
compounds that decompose to alcohols.
• Secondary amines: Forms nitrosamines (R₂N–NO).

Example Reaction:
Aniline (C₆H₅NH₂) + NaNO₂ + HCl (0–5 °C) Benzene diazonium chloride
(C₆H₅N₂⁺Cl⁻).

Key Notes:
• Diazonium salts are intermediates for azo dyes and Sandmeyer
reactions.

24. PCC (Pyridinium Chlorochromate)

• Reacts with:
• Primary alcohols: Oxidizes to aldehydes (stops at the aldehyde
stage).
• Secondary alcohols: Oxidizes to ketones.
• Does NOT oxidize tertiary alcohols.

Example Reaction:
Ethanol (CH₃CH₂OH) + PCC Acetaldehyde (CH₃CHO).

Key Notes:
• Milder than chromic acid (H₂CrO₄).
• Ideal for selective oxidation in organic synthesis.

25. CrO₃ + H₂SO₄ (Jones Reagent)

• Reacts with:
• Primary alcohols: Oxidizes to carboxylic acids.
• Secondary alcohols: Oxidizes to ketones.
• Does NOT react with tertiary alcohols.

Example Reaction:
Ethanol (CH₃CH₂OH) + CrO₃/H₂SO₄ Acetic acid (CH₃COOH).

Key Notes:
• A strong oxidizing agent; not suitable for sensitive molecules.
26. HIO₄ (Periodic Acid)
• Reacts with:
• Vicinal diols (1,2-diols): Cleaves them into aldehydes or
ketones.
• α-hydroxy ketones and α-hydroxy aldehydes: Cleaved into
carboxylic acids.

Example Reaction:
Ethane-1,2-diol (CH₂OH–CH₂OH) + HIO₄ Formaldehyde (HCHO) + Formic
acid (HCOOH).

Key Notes:
• Very speci c for vicinal diols.

27. H₂, Lindlar Catalyst

• Reacts with:
• Alkynes: Hydrogenates selectively to cis-alkenes.
• Does NOT fully hydrogenate alkynes to alkanes.

Example Reaction:
Phenylacetylene (C₆H₅C≡CH) + H₂ + Lindlar catalyst Styrene
(C₆H₅CH=CH₂).

Key Notes:
• Stops at the alkene stage; stereospeci c (cis only).

28. BH₃·THF (Borane in Tetrahydrofuran)

• Reacts with:
• Alkenes: Hydroboration-oxidation gives anti-Markovnikov
alcohols.
• Alkynes: Forms organoboranes, which can be converted to
aldehydes or ketones.

Example Reaction:
Propene (CH₃CH=CH₂) + BH₃·THF Propylborane, followed by H₂O₂/NaOH
1-Propanol (CH₃CH₂CH₂OH).

Key Notes:
• Highly regioselective for anti-Markovnikov addition.

29. O₃ (Ozone)
• Reacts with:
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 • Alkenes: Cleaves them into carbonyl compounds (aldehydes or
ketones).
• Alkynes: Cleaves them into carboxylic acids.

Example Reaction:
Ethene (CH₂=CH₂) + O₃ Formaldehyde (HCHO).

Key Notes:
• Often followed by reductive workup (e.g., Zn/H₂O) or oxidative workup
(e.g., H₂O₂).

30. NaOEt (Sodium Ethoxide)

• Reacts with:
• β-keto esters and malonic esters: Acts as a base for enolate
formation in Claisen condensation.
• Alkyl halides: Performs E2 elimination reactions.

Example Reaction:
Ethyl acetate (CH₃COOCH₂CH₃) + NaOEt Enolate intermediate Claisen
condensation product.

Key Notes:
• Strong base; used in anhydrous conditions.

31. Dess-Martin Periodinane (DMP)

• Reacts with:
• Primary alcohols: Oxidizes to aldehydes.
• Secondary alcohols: Oxidizes to ketones.

Example Reaction:
Benzyl alcohol (C₆H₅CH₂OH) + DMP Benzaldehyde (C₆H₅CHO).

Key Notes:
• Milder and more selective than PCC.

32. Raney Nickel (Ni)

• Reacts with:
• C=C bonds in alkenes: Hydrogenation to alkanes.
• C≡C bonds in alkynes: Hydrogenation to alkanes.
• Sulfur-containing compounds: Reduces thioketones and
sul des.
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Example Reaction:
Cyclohexene (C₆H₁₀) + H₂ + Raney Ni Cyclohexane (C₆H₁₂).

Key Notes:
• Works under high temperature and pressure.

33. SeO₂ (Selenium Dioxide)

• Reacts with:
• Allylic compounds: Oxidizes to allylic alcohols.
• Ketones: Oxidizes to α-diketones.

Example Reaction:
Cyclohexanone + SeO₂ 1,2-Cyclohexanedione.

Key Notes:
• Used for selective oxidation in allylic systems.

34. AlCl₃ (Aluminium Chloride)

• Reacts with:
• Aromatic compounds: Catalyzes Friedel-Crafts alkylation and
acylation.
• Carbocations: Stabilizes them for nucleophilic attack.

Example Reaction:
Benzene + Acetyl chloride + AlCl₃ Acetophenone (C₆H₅COCH₃).

Key Notes:
• Incompatible with water or alcohols.

Let’s keep going! Here are more important reagents with detailed
explanations, focusing on their reactivity and speci c molecule types:

35. NaBH₃CN (Sodium Cyanoborohydride)

• Reacts with:
• Imines (C=N): Reduces them to amines in reductive amination
reactions.
• Ketones and Aldehydes: Selectively reduces them to alcohols
under mild conditions.

Example Reaction:
Acetone (CH₃COCH₃) + Ammonia + NaBH₃CN Isopropylamine
(CH₃CH(NH₂)CH₃).
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Key Notes:
• Milder than NaBH₄ or LiAlH₄, used in aqueous or protic solvents.
• Does NOT react violently with water or alcohols.

36. NaH (Sodium Hydride)

• Reacts with:
• Alcohols: Deprotonates to form alkoxide ions.
• Carbonyl Compounds: Abstracts acidic α-hydrogens to form
enolate ions.
• Ethers: Used in Williamson ether synthesis.

Example Reaction 1:
Ethanol (CH₃CH₂OH) + NaH Sodium ethoxide (CH₃CH₂O⁻ Na⁺) + H₂.

Example Reaction 2:
Acetone (CH₃COCH₃) + NaH Enolate ion (CH₂⁻=C(O⁻)CH₃) + H₂.

Key Notes:
• A strong base; reacts explosively with water.
• Does NOT reduce carbonyl compounds like NaBH₄.

37. Br₂ in CCl₄ (Bromine in Carbon Tetrachloride)

• Reacts with:
• Alkenes: Adds bromine across the double bond to form dibromo
compounds.
• Aromatic Compounds: Undergoes bromination in the presence
of a Lewis acid catalyst like FeBr₃.

Example Reaction:
Cyclohexene + Br₂/CCl₄ 1,2-Dibromocyclohexane.

Key Notes:
• Test for unsaturation: Decolorization of bromine indicates the presence
of alkenes.

38. Ph₃P (Triphenylphosphine) + CCl₄

• Reacts with:
• Alcohols: Converts them into alkyl chlorides (Appel reaction).

Example Reaction:
Ethanol (CH₃CH₂OH) + Ph₃P + CCl₄ Ethyl chloride (CH₃CH₂Cl) + Ph₃PO.
Key Notes:
• Mild conditions; avoids overreaction with sensitive compounds.

39. Ag₂O (Silver Oxide)

• Reacts with:
• Aldehydes: Oxidizes to carboxylic acids (used in the Tollens
reagent test).
• Alkyl halides: Used in nucleophilic substitution to form ethers.

Example Reaction 1:
Acetaldehyde (CH₃CHO) + Ag₂O Acetic acid (CH₃COOH).

Example Reaction 2:
Methyl iodide (CH₃I) + Ag₂O Dimethyl ether (CH₃OCH₃).

Key Notes:
• A mild oxidizing agent, doesn’t affect ketones or alkenes.

40. Fe/HCl (Iron and Hydrochloric Acid)

• Reacts with:
• Nitro Compounds (Ar–NO₂): Reduces to aromatic amines (Ar–
NH₂).

Example Reaction:
Nitrobenzene (C₆H₅NO₂) + Fe/HCl Aniline (C₆H₅NH₂).

Key Notes:
• Used for selective reduction under acidic conditions.

41. NH₂NH₂ + KOH (Wolff-Kishner Reduction)

• Reacts with:
• Ketones and Aldehydes: Reduces them to alkanes under basic
conditions.

Example Reaction:
Acetone (CH₃COCH₃) + NH₂NH₂ + KOH Propane (CH₃CH₂CH₃).

Key Notes:
• Does NOT affect carboxylic acids, esters, or nitriles.
• Works under harsh basic conditions, unlike Clemmensen reduction
(acidic).
42. Na₂Cr₂O₇ + H₂SO₄ (Sodium Dichromate)
• Reacts with:
• Primary Alcohols: Oxidizes to carboxylic acids.
• Secondary Alcohols: Oxidizes to ketones.

Example Reaction:
Cyclohexanol + Na₂Cr₂O₇ + H₂SO₄ Cyclohexanone.

Key Notes:
• A strong oxidizing agent; not selective for sensitive groups.

43. K₂CO₃ (Potassium Carbonate)

• Reacts with:
• Acids: Neutralizes acids to form corresponding salts.
• Phenols and Alkyl Halides: Promotes nucleophilic substitution in
ether synthesis.

Example Reaction:
Phenol + Benzyl bromide + K₂CO₃ Benzyl phenyl ether.

Key Notes:
• A mild base used in aqueous and organic reactions.

44. MnO₂ (Manganese Dioxide)

• Reacts with:
• Allylic Alcohols: Oxidizes to aldehydes or ketones.
• Benzylic Alcohols: Oxidizes to benzaldehydes or ketones.

Example Reaction:
Benzyl alcohol (C₆H₅CH₂OH) + MnO₂ Benzaldehyde (C₆H₅CHO).

Key Notes:
• Highly selective for allylic and benzylic alcohols; doesn’t affect other
alcohols.

45. CH₂N₂ (Diazomethane)

• Reacts with:
• Carboxylic Acids: Converts to methyl esters.
• Alkenes: Adds a methylene group to form cyclopropanes.

Example Reaction 1:
Acetic acid (CH₃COOH) + CH₂N₂ Methyl acetate (CH₃COOCH₃).
Example Reaction 2:
Cyclohexene (C₆H₁₀) + CH₂N₂ Cyclopropylcyclohexane.

Key Notes:
• Toxic and explosive; used with extreme caution.

46. K₂Cr₂O₇ (Potassium Dichromate)

• Reacts with:
• Primary Alcohols: Oxidizes to carboxylic acids.
• Secondary Alcohols: Oxidizes to ketones.

Example Reaction:
Ethanol (CH₃CH₂OH) + K₂Cr₂O₇ Acetic acid (CH₃COOH).

Key Notes:
• Strong oxidizing agent like Na₂Cr₂O₇.