Chapter 16/28 - Organic Synthesis Flashcards by Areej A

Q

Which reactions lengthen carbon chain?

A

Formation of nitriles
Alkylation
Acylation

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Q

How to obtain pure sample of organic product after reflux/distillation?

A

Separating funnel (denser layer at bottom)
Dry with anhydrous salt e.g. MgSO₄
Redistill and collect product at appropriate boiling point

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Q

Alkane to haloalkane?

A

UV light
Halogen

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Q

Alkene to alkane?

A

H₂
Ni catalyst

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Q

Alkene to haloalkane?

A

Hydrogen halide

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Q

Alkene to alcohol?

A

H₂O (steam)
H₃PO₄

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Q

Alcohol to alkene?

A

Heat
H₃PO₄

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Q

Haloalkane to nitrile?

A

NaCN
Ethanol

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Q

Haloalkane to amine?

A

NH₃
Ethanol

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Q

Alcohol to haloalkane?

A

Sodium halide
H₂SO₄

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Q

Haloalkane to alcohol?

A

NaOH_(aq)

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Q

Nitrile to amine?

A

H₂
Ni catalyst

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Q

Nitrile to carboxylic acid?

A

H₂O
HCl
Heat

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Q

Hydroxynitrile to amine?

A

H₂
Ni catalyst

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Q

Alcohol to ester?

A

Carboxylic acid and conc. H₂SO₄
OR
Acid anhydride

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Q

Ester to carboxylate?

A

OH^-
Heat

Q

Carboxylic acid to ester?

A

Alcohol
Concentrated H₂SO₄

Q

Ester to carboxylic acid?

A

Dilute acid
Heat

Q

Acyl chloride to ester?

A

Alcohol

Q

Acyl chloride to primary amide?

A

NH₃

Q

Acyl chloride to secondary amide?

A

Primary amine

Q

Acyl chloride to carboxylic acid?

A

H₂O

Q

Carboxylic acid to acyl chloride?

A

SOCl₂

Q

Primary alcohol to aldehyde?

A

K₂Cr₂O₇/H₂SO₄
Distil

Secondary alcohol to ketone?

K₂Cr₂O₇/H₂SO₄ Reflux

Aldehyde to carboxylic acid?

K₂Cr₂O₇/H₂SO₄ Reflux

Primary alcohol to carboxylic acid?

K₂Cr₂O₇/H₂SO₄ Reflux

Aldehyde to primary alcohol?

NaBH₄

Ketone to secondary alcohol?

NaBH₄

Ketone to hydroxynitrile?

NaCN H⁺

Aldehyde to hydroxynitrile?

NaCN H⁺

Benzene to nitrobenzene?

Concentrated H₂SO₄ Concentrated HNO₃

Nitrobenzene to phenylamine?

Tin (Sn) Concentrated HCl

Benzene to bromobenzne?

Br₂ Halogen carrier e.g. AlBr₃

Benzene to chlorobenzene?

Cl₂ Halogen carrier e.g. AlCl₃

Benzene to methylbenzene? (alkylation)

CH₃Cl Halogen carrier e.g. AlCl₃

Benenze to phenylethanone? (acylation)

Acyl chloride CH₃COCl Halogen carrier e.g. AlCl₃