Organic Synthesis Reactions Flashcards by Thomas Jarrett

Halogenoalkane -> alcohol + ppt

Hint:
- Reagents and conditions
- Reaction type

+AgNO₃ in ethanol
Heat

Nuclephilic substitution
(water acts as nucleophile)

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Halogenoalkane -> nitriles

Hint:
- Reagents and conditions
- Reaction type

+KCN in ethanol
HUR
Nucleophilic substitution

(cyanide ion acts as a nucleophile)
(method of increasing C chain length)

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Combustion (alkanes)

Hint:
- Complete and incomplete reaction equation
- Reagents

Complete:
alkane + oxygen(excess) -> carbon dioxide + water

Incomplete:
alkane + oxygen(insufficient) -> carbon/carbon monoxide + water

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Free Radical Substitution

Hint:
- Reaction (overall)
- Reagents and conditions

Alkane + halogens -> halogenalkane

UV light + X₂

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Alkene -> Alkane

Hint:
- Reagents and conditions
- Reaction type

+Hydrogen
Solid nickel catalyst
150*C

Reduction hydrogenation

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Alkenes -> dihalogenoalkanes

Hint:
- Reagents and conditions
- Reaction type
- Colour change

+X₂ and RTP

Electrophilic addition

Halogen colour -> colourless

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Alkenes -> alcohols

Hint:
- Reagents and conditions
- Reaction type

solid H₃PO₄ catalyst
300*C and 60-70atm
electrophilic addition

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Alkene -> diol

Hint:
- Reagents and conditions
- Colour change
- Reaction type

KMnO₄ (aq)
dilute H₂SO₄
RTP
purple to colourless
oxidation / electrophilic addition

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Halogenoalkanes -> amines

Hint:
- Reagents and conditions
- Reaction type

excess NH₃ in ethanol
heat under pressure in sealed tube
nucleophilic substitution

(furher substitution may occur)
(ammonia molecule acts as a nucleophile)

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Halogenoalkanes -> alkenes

Hint:
- Reagents and conditions
- Reaction type

KOH in ethanol
Heat under reflux
Elimination

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Alcohol combustion

Hint:
- Reaction equation

Alcohol + oxygen -> water + carbon dioxide

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Alcohol -> ketone (acidic)

Hint:
- Type of alcohol
- Reagents and conditions
- Colour change
- Reaction type

2* alcohol
[O] -> K₂Cr₂O₇
dilute H₂SO₂
Heat under reflux then distill out
Oxidation
Orange to green

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Alcohol -> halogenoalkane

Hint:
- Reagents and conditions (for each halogen)
- Reaction type

Chloro -> +PCl₅
Iodo -> Red phosphorus + 3/2 I₂
Bromo -> KBr + 50% conc H₂SO₄
Substitution

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Alcohol -> aldehyde (acidic)

Hint:
- Type of alcohol
- Reagents and conditions
- Colour change
- Reagents

1* alcohol
[O] -> K₂Cr₂O₇
dilute H₂SO₄
Oxidation
Orange -> green
Warm gently and distill out as it forms

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Aldehyde -> carboxylic acid (acidic)

Hint:
- Reagents and conditions
- Reaction type
- Colour change

[O] -> K₂Cr₂O₂
dilute H₂SO₂
Heat under reflux
Oxidation
Orange to green
Distil out acid

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Alcohol -> carboxylic acid (acidic)

Hint:
- Alcohol type
- Reagents and conditions
- Reaction type
- Colour change

2[O] -> K₂Cr₂O₇
Dilute H₂SO₄
Heat under reflux
Orange -> green

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Alcohol -> alkenes

Hint:
- Reagents and conditions
- Reaction type

H₃PO₄ catalyst
Warm under reflux
Elimination

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Alkene -> polymer

Hint:
- Reagents and conditions
- Reaction type

Addition polymerisation
High temp + pressure
(exact conditions depends on alkene)

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Halogenoalkane -> alcohol

Hint:
- Reagents and conditions
- Reaction type

KOH
Heat under reflux
Nucleophilic substitution

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Acyl chloride + alcohol -> ester

Hint:
- Side product
- Advantages
- Reaction type

HCl
Esterification
Fast and irreversible therefore high yield

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Acyl chloride -> cab rboxylic acid

Hint:
- Reagents and conditions
- Side product and hazard

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water
HCl
very acidic as two acids are produced (HCl + COOH)

Carboxylic acid + alcohol -> ester

Hint:
- Reaction type
- Reagents and conditions

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Condensation esterification
conc H₂SO₄ catalyst

Carboxylic acid -> acyl chloride

Hint:
- Products
- Respective observations
- Reagents
- Reaction type

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PCl₅
Products HCl and POCl₃ (HCl in the form of steamy white fumes + effervescence)
Substitution

Nitrile -> carboxylic acid

Hint:
- Reagents and conditions
- Reaction type
- Reaction equation

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R-CN + 2H₂O -> carboxylic acid or carboyxlate salt
Heat under reflux w/:
NaOH -> salt
dilute HCl -> acid
Produces ammonia/ammonium dependent on conditions
Nitrile hydrolysis/Substitution

Acyl chloride -> amide Hint: - Side products - Reagents and conditions - Reacton type

- ammonia - HCl produced - Condensation

Acyl chloride -> N-substituted amide Hint: - Reagents and conditions - Side products

- amine - produces HCl

Ester -> carboxylic acid + alcohol (acidic) Hint: - Reagents and conditions - Disadvantages

- H2O - H⁺ catalyst (dilute HCl(aq)) - Heat under reflux - Sow and reversible therefore no yield

Aldehyde -> carboxylate (Fehling's/Benedict/s) Hint: - Reagents and conditions - Colour change - Reaction type

- Fehling's/Benedict's solution (alkaline Cu2⁺ ions) - Blue solution -> red precipitate - alkaline oxidation

Aldehyde -> carboxylate (Tollens') Hint: - Reagents and conditions - Observations - Reaction type

- Alkaline Ag⁺ (aq) - Forms silver mirror - Alkaline oxidation

Ester -> carboxylic acid + alcohol (alkanline) Hint: - Reagents and conditions - Advantage

- NaOH - Warm - Fast, irreversible and therefore has a high yield - Add HCl after to turn the carboxylate salt formed into a carboxylic acid

Polyester formation Hint: - Reaction pairs - Respective reaction type and products

- Dicarboxylic acid + diol -> water - Diacyl chlroide + diol -> HCl - Hydroxycarboxylic acid -> water - Hydroxyacylchloride -> HCl - Condensation esterification polymerisation

Aldeyde/ketone -> nitrile Hint: - Reagents and conditions (+explanation) - Reaction type

- HCN + KCN - KCN needed to generate nucleophile and HCN needed to turn C=O -> C-OH - Nucleophilic substitution

Aldehyde -> 1* alcohol Hint: - Reagents and conditions - Reaction equation - Reaction type

Aldehyde + 2[H] -> 1* alcohol [H] -> Lithal: lithium aluminium tetrahydride (solvent: dry ether) -then dilute HCl (aq) -reduction

Ketone -> 2* alcohol Hint: - Reagents and conditions - Reaction equation - Reaction type

Ketone + 2[H] -> 2* alcohol [H] -> Lithal: lithium aluminium tetrahydride (solvent: dry ether) -then dilute HCl (aq) -reduction

Carboxylic acid -> 1* alcohol Hint: - Reagents and conditions - Reaction equation - Reaction type

Carboxylic acid + 4[H] -> 1* alcohol [H] -> Lithal: lithium aluminium tetrahydride (solvent: dry ether) -then dilute HCl (aq) -reduction

Iodoform reaction Hint: - Reagents and conditions - Observations - Reaction equation (+ product structure) - Possible reactants

iodine + methyl ketone or methyl 2* alcohol -> iodoform - I₂ (aq) w/ NaOH (aq) - warm - iodoform [RCOO-] - pale yellow ppt + antiseptic smell

Nitrile -> amine Hint: - Reaction type (2) - Reagents and conditions (2)

- Reduciton via hydrogenation - LiAlH4 + acidic conditions OR - Catalytic hydrogenation - H₂ w/ nickel catalyst

Friedel-Crafts Acylation Hint: - Reaction equation - Reagents and conditions

Benzene + R-COCl -> Benzene-C-RO + HCl - Acyl chloride - Warm w/ AlCl3 catalyst

Phenol -> tribromophenol Hint: - Reagents and conditions

- Br₂ - no heat, no catalyst

Halogenoalkane -> amine Hint: - Reaction type - Reaction equation - (explanation for low yield)

- Nucleophilic substitution - RX + 2NH₃ -> R-NH₃ + NH₄⁺ +X^- - Substitution can occur w/ all hydrogens on the amine because the product is still a nucleophile due to the lone pair on the nitrogen

Amine + Cu²⁺ Hint: - Reaction equation

[Cu(H₂O)₆]²⁺ + 2 R-NH₂ -> [Cu(H₂O)₄(OH)₂] + 2 R-NH₃⁺

Amine -> salt Hint: - Reaction equation - Salt produced

R-NH₂ + HCl -> R-NH₃⁺ - Ammonium salt produced

Amine -> amide Hint: - Reaction equation - Structure of possible products

Amine + acyl chloride -> amide/N-sub amide Amide -> R-CONH₂ N-sub amide -> R-CONHR

Friedel-Crafts Alkylation Hint: - Reaction equation - Reagents and conditions

Benzene + R-Cl -> Beneze-R + HCl - Warm w/ R-Cl + AlCl₃ catalyst

Benzene combustion Hint: - Reaction equation - Observation + explanation

Benzene + O₂ -> CO₂/C + H₂O - Sooty flame - Because easier to produce elementary carbon

Grignard reagents Hint: - Reagents and conditions - Side product - Reaction type - Possible reactions

R-MgBr + H⁺ -> MgBr⁺ - Nucleophilic addition - R-MgBr in dry ether Possible Reactions: 1. Methanol -> 1* alcohol 2. Aldehyde -> 2* alcohol 3. Ketone -> 3* alcohol 4. CO₂ -> carboxylic acid

Polyamide produciton Hint: - Reaction pairs

Diamines + diacyl chloride Amine carboxylic acid Dicarboxylic acid + diamines Amine acyl chloride

Benzene -> benzene nitrate Hint: - Reagents and conditions - Mechanism steps

- Conc H₂SO₄ catalyst - Conc HNO₃ - Warm but T < 50*C - Mechanism: 1. Generate electrophile 2. Substitution 3. Cleaning up

Amine -> base Hint: - Reaction equation - Explanation

R-NH₂ + H₂O -> R-NH₃⁺ + OH^- - Amine acts as base due to lone pair on nitrogen accepting H⁺

Benzene -> bromobenze Hint: - Mechanism steps - Reagents and conditions

- Warm w/ Br₂ + AlBr₃ catalyst - Mechanism: 1. Generate electrophile 2. Substitution 3. Cleaning up

Organic Synthesis Reactions Flashcards

(50 cards)