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Ochem Two > Test 2 reactions > Flashcards

Test 2 reactions Flashcards

1
Q

Carboxylic Acid——-> Acid Halide

A 
PX3, Pyridine
heat
OR
SOCl2, pyridine
heat
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2
Q

Acid halide——> anhydride

A

Carboxylate

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3
Q

Acid Halide——-> ester

A

Alcohol

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4
Q

Acid Halide——-> Amide

A

2 eq amine

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5
Q

Acid Halide——-> carboxylic acid

A

H2O

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6
Q

2 carboxylic acid ——> anhydride

A

P2O5
or
heat

(remove H2O)

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7
Q

Anhydride——–> Ester

mixture of esters

A

alcohol

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8
Q

Anhydride——-> Amide

A

2 eq amine

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9
Q

Hydrolysis of anhydride

A

H2O

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10
Q

Carboxylate——–> ester

A

PRIMARY alkyl halide

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11
Q

Carboxylic Acid——–> ester

A

DCC

Alcohol

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12
Q

Fisher Esterification:

Carboxylic acid——–ester

A

alcohol in the presence of an acid

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13
Q

Transesterification:

Ester———> new Ester

A

alcohol in the presence of an acid

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14
Q

Ester———> Amide

A

amine

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15
Q

Acid catalyzed hydrolysis of an ester

A

H2O
H+
(reversible)

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16
Q

Acid catalyzed hydrolysis of the tertiary alkyl ester

A

H2O
H+
(Sn1)

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17
Q

Base catalyzed hydrolysis of an ester

Saponification

A

NaOH
H2O
(not reversible)

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18
Q

Carboxylic Acid———> Amide

A

DCC

an Amine

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19
Q

Amide———-> ester

A

Alcohol
Heat
(in acidic conditions)

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20
Q

Amide———> Nitrile

A

thionyl chloride

SOCl2

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21
Q

Base Catalyzed hydrolysis of Amide

A
  1. NaOH H2O

2. H+

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22
Q

Acid catalyzed hydrolysis of Amide

A

H2O

H+

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23
Q

Gabriels Amine Synthesis:

Creates Primary Amine

A
  1. NaOH
  2. Alkyl Halide
  3. HCl, H2O
  4. NaOH
24
Q

Alkyl Halide————> Nitrile

A

Cyanide

CtriplebondN

25
Q

Acid Catalyzed hydrolysis of Nitrile

A

H2O,HCl

Heat

26
Q

formaldehyde———->primary alcohol

A
  1. Grignard reagent

2. H3O+

27
Q

Aldehyde———-> Secondary alcohol

A
  1. Grignard Reagent

2. H3O+

28
Q

Ketone———> Tertiary Alcohol

A
  1. Grignard reagent

2. H3O+

29
Q

ester OR acyl halide——-> tertiary alcohol

A
  1. 2 eq Grignard reagent
  2. H2O

(product will have 2 identical substituents)

30
Q

The Silyl Ether protecting group

Protects the OH

A

TMS-Cl
imidazole

(TBDMS-Cl)

31
Q

Addition of Acetylide Anion

Ketones & Aldehydes

A
  1. Acetylide Anion ( -CtripleCCH3)

2. pyridinium chloride

32
Q

Ketone/aldehyde——-> cyanohydrin

33
Q

Acid Halide———> Primary alcohol

A
  1. 2 eq NaBH4

2. H2O

34
Q

Acid Halide———-> Aldehyde

A
  1. LiAl[OC(CH3)3}3H -78degC

2. H2O

35
Q

Aldehyde——–> Primary Alcohol

A
  1. NaBH4

2. H3O+

36
Q

Ketone——-> Secondary Alcohol

A
  1. NaBH4

2. H3O+

37
Q

Ester———-> Primary Alcohol

A
  1. 2 eq LiAlH4

2. H3O+

38
Q

Ester———> Aldehyde

A
  1. DIBALH -78degC

2. H2O

39
Q

Carboxylic Acid————> Primary Alcohol

A
  1. 2 eq LiAlH4

2. H3O+

40
Q

Amide——–> Amine

A
  1. LiAlH4

2. H2O

41
Q

Nitriles——–>primary amine

A
  1. NaBH4
  2. H2O
    OR
    H2, Raney Ni
42
Q

Imine———-> Secondary Amine

A
  1. NaBH4
  2. H2O
    OR
    H2, Raney Ni
43
Q

Aldehyde/Ketone————> Imine

A

Primary amine, H+ (trace)

reversible with H3O+

44
Q

imine———-> secondary amine

A

NaBH3CN

OR

H2, Pd/C

45
Q

Aldehyde/Ketone————> Enamine

A

Secondary amine, H+ (trace)

reversible with H3O+

46
Q

Enamine———> tertiary amine

A

NaBH3CN

OR

H2, Pd/C

47
Q

Aldehyde/Ketone————> Hemiacetal

A

1 eq alcohol

reverses with H3O+

48
Q

Aldehyde/Ketone————>Acetal

A

2 eq alcohol

reverses with H3O+

49
Q

Ketone———> ester

A

peroxyacid

50
Q

Aldehyde———> carboxylic acid

A

peroxyacid

51
Q

aldehyde/ketone———-> thioacetal

A

2 eq thiol

52
Q

alkylation of thioacetal

A
  1. nBuLi

2. alkyl halide

53
Q

Hydrogenation of thioacetal

A

H2 Raney Ni

54
Q

Primary alkyl halide——-> Wittig

A
  1. PPh3

2. nBuLi

55
Q

Aldehyde/ketone——> alkene

A

WIttig reagent

Ochem Two (1 decks)

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