AQA A-level Chemistry: Organic Synthesis Routes

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How Do You Convert An Alkene To An Alkane?

H2, Ni catalyst, 150°C

How Do You Make A Haloalkane From An Alkane?

(Alkane —> Haloalkane)

X2, UV light

How Do You Make An Alkene From A Haloalkane?

(Haloalkane —> Alkene)

KOH, ethanol, reflux

How Do You Make A Haloalkane From An Alkene?

(Alkene —> Haloalkane)

HX, 20°C

How Do You Make An Alcohol From A Haloalkane?

(Haloalkane —> Alcohol)

Warm NaOH, H2O, reflux

How Do You Make A Haloalkane From An Alcohol?

(Alcohol —> Haloalkane)

NaX, H2SO4, 20°C

How Do You Make An Alcohol From An Alkene?

(Alkene —> Alcohol)

Steam, H3PO4, catalyst, 60 atm, 300°C

How Do You Make An Alkene From An Alcohol?

(Alcohol —> Alkene)

Concentrated H2SO4 / H3PO4, heat

How Do You Make A Dihaloalkane From An Alkene?

(Alkene —> Dihaloalkene)

X2 + 20°C

How Do You Make An Aldehyde From An Alcohol?

(Alcohol —> Aldehyde)

K2Cr2O7 (Potassium dichromate), H2SO4, Primary alcohol, all in a distillation kit.

How Do You Make A Ketone From An Alcohol?

(Alcohol —> Ketone)

K2Cr2O7 (Potassium dichromate), H2SO4, heat, and Secondary alcohol

Condition: Reflux

How Do You Make A Secondary Alcohol From A Ketone?

(Ketone —> Alcohol)

NaBH4, in methanol + H2O

How Do You Make A Primary Alcohol From An Aldehyde?

(Aldehyde —> Alcohol)

NaBH4, in methanol + H2O

How Do You Make A Carboxylic Acid From An Aldehyde?

(Aldehyde —> Carboxylic Acid)

K2Cr2O7 (Potassium dichromate), H2SO4, reflux

How Do You Make A Nitrile From A Haloalkane?

(Haloalkane —> Nitrile)

KCN, ethanol, reflux

How Do You Make A Primary Amine From A Nitrile?

(Nitrile —> Primary Amine)

LiAlH4 + Dilute H2SO4

How Do You Make A Primary Amine From A Haloalkane?

(Haloalkane —> 1° amine)

NH3 + heat

How Do You Make A Hydroxynitrile From An Aldehyde/Ketone?

(Aldehyde/Ketone —> Hydroxynitrile)

KCN, H2SO4, 20°C

How Would You Make An Ester From A Carboxylic Acid?

(Carboxylic Acid —> Ester)

Concentrated H2SO4, alcohol, heat, and catalyst

How Do You Make A Carboxylic Acid From An Ester?

(Ester —> Carboxylic Acid)

Dilute H2SO4, H2O, reflux, catalyst

\
OR

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Dilute NaOH, reflux

How Do You Make A Carboxylic Acid From An Acyl Chloride / Acid Anhydride?

(A.C/A.A —> Carboxylic Acid)

Water + 20°C/heat

How Do You Make An Ester From An Acyl Chloride/Acid Anhydride?

(A.C/A.A —> Ester)

Alcohol + 20°C

How Do You Make A Primary Amide From An Acyl Chloride / Acid Anhydride?

(A.C/A.A —> Primary Amide)

NH3 + 20°C

How Do You Make An N-Substituted Amide From An Acyl Chloride / Acid Anhydride?

(A.C/A.A —> N-Sub. Amide)

Amine + 20°C

How Is A Nitrobenzene Formed From A Benzene?

__Nitration__

Concentrated H2SO4 + HNO3; < 55°C to avoid multiple substitutions (explosive)

How Is A Phenylketone (R-C=O Attached To Benzene From C) Formed From A Benzene?

__Acylation__

RCOCl (acyl chloride), AlCl3 catalyst, reflux, anhydrous conditions

How Is A Phenylamine Formed From A Nitrobenzene?

__Reduction__

Concentrated HCl, Sn, reflux + add NaOH

How Is An N-Phenylethamide Formed From A Phenylamine?

CH3COCl + room temperature

Outline The Pathway From Benzene To The Formation Of N-Phenylethanamide

1. Nitration (Conc. H2SO4 + HNO3,

Why Are Organic Synthesis Routes Important?

Used to make drugs:


1. Cost effective
2. Safe (goal of low toxicity)
3. Have minimal environmental impact (high atom economy + % yield preferred; routes with less steps - less waste - more efficient)

Why Do Chemists Try To Minimise Or Avoid The Use Of Solvents In Chemical Reactions?

Because solvents are often flammable and toxic, and increase waste.

Why Is KCN Used Instead Of HCN In Reactions Involving Aldehydes Or Ketones?

Because HCN is a toxic gas and thus can be harmful.

What Are The Risks Associated With Using KCN In Reactions Involving Aldehydes And Ketones?

KCN is an irritant, dangerous if ingested or inhaled.

When reacting with moisture it can also form HCN, a toxic gas.