Chapter 28 - Organic Synthesis Flashcards

1
Q

How can you form a nitrile from a haloalkane?

A

React KCN or NaCN with haloalkane in ethanol.

for example: 1-chloropropane + KCN -> butanenitrile .

The mechanism is nucleophillic substitution.

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2
Q

How can you form a nitrile from an aldehyde or ketone?

A

Aldehydes and ketones react with HCN by nucleophillic addition to form a hydroxynitrile.

HCN is too dangerous to be used in labs so is replaced with NACN and Sulfuric acid.

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3
Q

what are nitriles reduced to?

A

Nitriles can be reduced to amines by reacting it with hydrogen in the presence of nickel catalyst.

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4
Q

What are the products for the hydrolysis of nitriles?

A

Nitriles under hydrolysis to form carboxylic acids by heating with aqeouas acid eg HCL.

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5
Q

How to turn Alkene to alkane?

A

H2 + nickel catalyst

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6
Q

Alkene to haloalkane?

A

Hydrogen halide

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7
Q

Alkene to alcohol?

A

Steam + H3PO4 catalyst

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8
Q

Alcohol to alkene?

A

H3PO4 + heat

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9
Q

Alkane to haloalkane?

A

Halogen + UV

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10
Q

Haloalkane to nitrile?

A

NaCN + ethanol

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11
Q

Haloalkane to amine?

A

Ammonia +ethanol

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12
Q

Haloalkane to alcohol?

A

NaOH + reflux

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13
Q

Alcohol to haloalkane?

A

Sodium halide + H2SO4

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14
Q

Alcohol to aldehyde?

A

Primary alcohol + acidified potassium dichromate + distil

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15
Q

Alcohol to Carboxylic acid?

A

Primary alcohol + acidified potassium dichromate + reflux

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16
Q

Alcohol to ketone?

A

Secondary alcohol + acidified potassium dichromate +reflux

17
Q

Aldehyde/ketone to hydroxynitrile?

A

NaCN + H+

18
Q

Nitrile to carboxylic acid?

A

H2O + HCL + heat

19
Q

Alcohol to ester?

A

React with carboxylic acid/ acid anhydride/acyl chloride + H2SO4 +heat

20
Q

Carboxylic acid to ester?

A

Alcohol + conc H2SO4 + heat

21
Q

Carboxylic acid to acyl chloride?

A

SOCl2

22
Q

Acyl chloride to carboxylic?

A

H2O

23
Q

Acyl chloride to primary amine?

A

NH3

24
Q

Acyl chloride to secondary amide?

A

Primary amine

25
Q

Benzene to bromobenzene?

A

Br2 + AlBr3/FeBr3

26
Q

Benzene to chlorobenzene?

A

Cl2 + AlCl3/FeCl3

27
Q

Benzene to alkylbenzene?

A

Alkyl chloride + AlCl3

28
Q

Benzene to nitrobenzene?

A

Conc HNO3 + Conc H2SO4 + heat to 55 degrees.

29
Q

Nitrobenzene to phenylamine?

A

Sn/ conc HCl

30
Q

Phenol to nitrophenol?

A

Dilute HNO3

31
Q

Phenol to sodium phenoxide?

A

NaOH(aq)

32
Q

Phenol to bromphenol?

A

Br2

33
Q

Aldehydes/ketones to alcohols?

A

NaBH4