Organic Synthesis Flashcards by Anthony Royster

Q

A

Electrophilic addition
Conc H3PO4 Catalyst
Steam
60-70 ATM of pressure
200-450 degrees

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Q

A

Elimination
Conc H2SO4 Catalyst
Under Reflux

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Q

A

Hydrogenation
H2
Nickel Catalyst

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Q

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Elimination
KOH
Hot & Ethanoic Conditions

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Q

A

Electrophilic Addition
HX (Where x = Halogen)
20 Degrees

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Q

A

Free Radical Substitution
X2 (where x is a halogen)
UV Light

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Q

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(Don’t need at this level)
Elimination
XBr

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Q

A

Nucleophilic Substitution
KOH
Cold and Aqueous

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Q

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Nucleophilic Addition (Reduction)
NaBH4 or LiAlH4 Reducing agents

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Q

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Oxidisation
H+ or Acidified Potassium Dichromate

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Q

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Oxidisation
H+ or Acidified Potassium Dichromate

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Q

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Esterification
:OH - (alcohols)
Strong Acid Catlayst

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Q

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Esterification
Acid Anhydride or Acyl Chloride
String Acid catalyst

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Q

A

Nucleophilic Addition Elimination
:OH- (alcohols)

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Q

A

Nucleophilic Addition Elimination (Hydrolysis)
H2O

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Q

A

Nucleophilic Addition Elimination
:NH3 or Amines

Q

A

Nucleophilic Addition Elimination
Acid Anhydride or Acyl Chloride

Q

A

Nucleophilic Subsitiution
KCN
Aqueous Ethanoic Conditions

Q

A

Nucleophilic Addition
H2 Nickel Catalyst
or
LiAlH4

Q

A

Nucleophilic Subsitution
Excess Conc :NH3
Ethanoic
Heat with Sealed System/Container

Q

What is Organic Synthesis

A

Using reaction mechanisms to create a target molecule

Q

Why is it preferable to create a molecule with as little steps as possible

A

To improve the % yield of the Product

Q

What Could Cause the yield of an individual step to be low? (2)

A

Chemicals are lost when transferring between containers - some product could be left in the refraction mixture each time

Incomplete/ reversible reactions

Q

What are the two main dehydrating agents used?

A

Al2O3 (Vapours pass over it)

Acid-Catalysed elimination (Strong acid catalysts)

What does a smoky flame when burnt suggest

High C:H ratio (possibly aromatic)

What are the 3 main reducing agents used? What do they Reduce?

NaBH4 —> Reduces C=O (Hydride H- attacks delta positive carbon) H2/Ni Catalyst —-> Reduces C=C HCl/Tin + small amount of NaOH—-> Reduces NO2 to NH2

Name the Mechanism/Reaction Type, reactants and conditions

Electrophilic Substitution

Name the Mechanism/Reaction Type, reactants and conditions

Reduction

Name the Mechanism/Reaction Type, reactants and conditions

Nucleophilic addition Elimination Acid Anhydride or Acyl Chloride

Name the Mechanism/Reaction Type, reactants and conditions

Electrophilic substitution AlCl3 Catalyst Acyl Chloride or Acid anhydride

Name the Mechanism/Reaction Type, reactants and conditions

Name the Mechanism/Reaction Type, reactants and conditions

How would you test for Acyl Chloride

Add Water, White misty fumes of HCl

Describe the differences with an OH- acid and OH- Alcohol infrared spectra

OH- acid has its lowest point of the broad peak below 3000cm^-1 (and a C=O sharp peak) OH- alcohol is more rounded and has its peak above 3000cm^-1

Explain how you would synthesise the following amine, with methylbenzene as your starting molecule

Step 1 : Use FRS to form Bromo-methylbenzene Br2 and UV light Step 2: Nucleophilic substitution of KCN alcoholic and aqueous conditions Step 3: H2/Nickel catalyst (Reduction)