Exam 4 Hilinski Reactions

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Last updated 5:21 PM on 4/11/26
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32 Terms

1
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Carboxylic —> Deprotenated w/ anion

NaOH ; H2O

2
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Carboxylic —> Deprotenate

H2O

3
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alkyl —> Carboxylic

KMnO4 ; H2O heat

4
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1 OH —> carbox

KMnO4

5
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aldehyde —> carbox

KMnO4/H2O ; NaOH

6
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aldehyde —> ether + CN

NaCN, H2O ; H2SO4, H2O

7
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1 Halogen —> nitrile

NaCN

8
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Nitrile —> carboxylic

NaOH, H2O ; H2SO4, H2O (only step 1 = deprote)

9
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Carboxylic —> 1 OH

1.LiAlH4, diether ; 2.H2SO4, H2O

10
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Carboxylic —> Acid Chloride

SOCl2 ; CHCl3

11
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Acid chloride —> ester

ROH ; HCl

12
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Acid Chloride —> 1 amide

RNH2

13
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Amide —> carboxylic

H2SO4, H2O

14
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Amide —> Nitrile

SOCl2, benzene ; heat

15
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Nitrile —> Ketone

  1. RMgBr, ether ; 2. H2SO4, H2O

16
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Nitrile —> Amine

  1. LiALH4, diether ; 2. H2SO4, H2O

17
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Nitrile —> Amide

H2SO4, H2O

18
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2 x Carboxylic —> Acid Anhydride

heat

19
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Deprote Carboxylic —> Ester

CH3I

20
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21
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Carboxylic —> Ester

ROH ; H2SO4, heat

22
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Carbox + Ketone —> Ketone

heat

23
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Ester —> Carboxylic salt + 1 OH (Basic)

NaOH, H2O ; heat

24
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Ester —> carboxylic + 1 OH (Acidic)

H2SO4, H2O ; heat

25
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Acid chloride —> 2 amide

2 x HN(CH2CH3)2

26
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2 Amide —> Carboxylic + Ammonium (Acidic)

H2SO4, H2O ; heat

27
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2 Amide —> Carboxylic salt + amine (Basic)

NaOH, H2O ; heat

28
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Carboxylic + OH —> deprotenate just carbox

NaHCO3 ; H2O

29
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Carbox + OH —> Deprotenate both

NaOH ; H2O

30
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Carboxylic —> methyl and 1 (Sub)

2 x Li(N 2xisoproyl)

31
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Carboxylic —> 2 and 3 (Elim)

2 x Li(N 2xisoproyl)

32
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Acid Chloride —> Ester

NaOCH3 ; CH3OH