ORGANIC SYNTHESIS Flashcards by Faizan Haider

Q

Alkane to Haloalkane

A

Free-radical halogenation

Conditions: UV light/heat

Example: CH₄ + Cl₂ → CH₃

Reagent: Cl₂ or Br₂

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Q

Alkene to Vicinal Dihalide

A

Halogen addition

Conditions: Room temp (no catalyst)

Example: CH

Reagent: X₂ (Br₂, Cl₂)

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Q

Vicinal Dihalide to Alkene

A

Dehydrohalogenation

Conditions: Heat

Example: CH₂BrCH₂Br → CH₂=CH

Reagent: KOH (alcoholic)

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Q

Alkene to Alkyne

A

Dehydrohalogenation → Alkyne

Conditions: High heat

Example: CH₂=CH₂ →

Reagent: NaNH₂ (strong base)

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Q

Alkyl Halide to Nitrile

A

Nucleophilic substitution

Conditions: Ethanol, heat

Example: CH₃CH₂Br + KCN →

Reagent: KCN/NaCN

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Q

Alkyl Halide to Alcohol

A

Hydrolysis

Conditions: Reflux

Example: CH₃CH₂Br + KOH → CH₃C

Reagent: Aqueous KOH

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Q

Alkyl Halide to Ether

A

Williamson Synthesis

Conditions: Dry ether

Example: CH₃CH₂B

Reagent: Sodium alkoxide (RONa)

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Q

Alkyl Halide to Amine

A

Ammonolysis

Conditions: Sealed tube, heat

Example: CH₃CH₂Br

Reagent: NH₃ (excess)

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Q

Alkyl Halide to Azide (RN₃)

A

Substitution with NaN₃

Conditions: Polar solvent (e.g., DMF)

Example: CH₃CH₂Br

Reagent: NaN₃

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Q

Nitrile to Carboxylic Acid

A

Acidic hydrolysis

Conditions: Reflux

Example: CH₃CN → CH₃COOH

Reagent: H₃O⁺ (HCl/H₂O)

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Q

Alcohol to Ether

A

Dehydration (Williamson)

Reagent: H₂SO₄ (conc.) or Na metal

Conditions

Dehydration (Williamson)

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Q

Secondary Alcohol to Ketone

A

Oxidation

Conditions: Heat

Example: (CH₃)₂CHOH →

Reagent: KMnO₄/K₂Cr₂O₇ (acidic)

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Q

Primary Alcohol to Aldehyde

A

Partial oxidation

Conditions: Anhydrous, room te

Reagent: PCC (Pyridinium Chlorochromate)

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Q

Aldehyde to Carboxylic Acid

A

Strong oxidation

Conditions: Heat

Example: CH₃CHO → CH₃

Reagent: KMnO₄/H⁺ or K₂Cr₂O₇/H⁺

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Q

Aldehyde to Amide

A

Reductive amination

Conditions: High pressure

Example: CH₃CHO → CH₃CO

Reagent: NH₃ + H₂/Pd

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Q

Carboxylic Acid to Acid Chloride

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A

Thionyl chloride

Conditions: Room temp

Example: CH₃COOH → CH₃COCl

Reagent: SOCl₂

Q

Acid Chloride to Amide

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A

Ammonolysis

Conditions: Cold

Example: CH₃COCl + NH₃ → CH₃CONH₂

Reagent: NH₃

Q

Aldehyde to Nitroalkane (RNO₂)

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A

Nef reaction

Conditions: Acidic medium

Example: CH₃CHO

Reagent: HNO₂ (nitrous acid)

Q

Ketone to Alcohol

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A

Reduction

Conditions: Dry ether

Example: (CH₃)₂CO → (CH

Reagent: NaBH₄ or LiAlH₄

Q

Amide to Amine

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A

Hoffmann degradation

Reagent: Br₂ + NaOH

Conditions: Heat

Example:

A: Hoffmann degradation

Q

Final Tips:

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A

Memorize reagents (e.g., LiAlH₄ for reductions, KMnO₄ for oxidations).

Conditions matter! (e.g., aqueous vs. alcoholic KOH).

Spot typos: “Hydroide” = hydroxide (OH⁻), “RNN3” = azide (N₃⁻).

You’re now ready to dominate organic synthesis! 🧪🔥

Q

Add Carbon

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A

R-BR + KCN –> R-CN + HBr

Alkyl halide + KCN -> RCN + HBr