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Ochem Two > Test 2 reactions > Flashcards

Test 2 reactions Flashcards

(55 cards)

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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

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

Alkyl Halide————> Nitrile

Study These Flashcards
A

Cyanide

CtriplebondN

25
Acid Catalyzed hydrolysis of Nitrile
H2O,HCl | Heat
26
formaldehyde---------->primary alcohol
1. Grignard reagent | 2. H3O+
27
Aldehyde----------> Secondary alcohol
1. Grignard Reagent | 2. H3O+
28
Ketone---------> Tertiary Alcohol
1. Grignard reagent | 2. H3O+
29
ester OR acyl halide-------> tertiary alcohol
1. 2 eq Grignard reagent 2. H2O (product will have 2 identical substituents)
30
The Silyl Ether protecting group | *Protects the OH*
TMS-Cl imidazole (TBDMS-Cl)
31
Addition of Acetylide Anion | Ketones & Aldehydes
1. Acetylide Anion ( -CtripleCCH3) | 2. pyridinium chloride
32
Ketone/aldehyde-------> cyanohydrin
HCN, KCN
33
Acid Halide---------> Primary alcohol
1. 2 eq NaBH4 | 2. H2O
34
Acid Halide----------> Aldehyde
1. LiAl[OC(CH3)3}3H -78degC | 2. H2O
35
Aldehyde--------> Primary Alcohol
1. NaBH4 | 2. H3O+
36
Ketone-------> Secondary Alcohol
1. NaBH4 | 2. H3O+
37
Ester----------> Primary Alcohol
1. 2 eq LiAlH4 | 2. H3O+
38
Ester---------> Aldehyde
1. DIBALH -78degC | 2. H2O
39
Carboxylic Acid------------> Primary Alcohol
1. 2 eq LiAlH4 | 2. H3O+
40
Amide--------> Amine
1. LiAlH4 | 2. H2O
41
Nitriles-------->primary amine
1. NaBH4 2. H2O OR H2, Raney Ni
42
Imine----------> Secondary Amine
1. NaBH4 2. H2O OR H2, Raney Ni
43
Aldehyde/Ketone------------> Imine
Primary amine, H+ (trace) *reversible with H3O+*
44
imine----------> secondary amine
NaBH3CN OR H2, Pd/C
45
Aldehyde/Ketone------------> Enamine
Secondary amine, H+ (trace) *reversible with H3O+*
46
Enamine---------> tertiary amine
NaBH3CN OR H2, Pd/C
47
Aldehyde/Ketone------------> Hemiacetal
1 eq alcohol | reverses with H3O+
48
Aldehyde/Ketone------------>Acetal
2 eq alcohol | reverses with H3O+
49
Ketone---------> ester
peroxyacid
50
Aldehyde---------> carboxylic acid
peroxyacid
51
aldehyde/ketone----------> thioacetal
2 eq thiol
52
alkylation of thioacetal
1. nBuLi | 2. alkyl halide
53
Hydrogenation of thioacetal
H2 Raney Ni
54
Primary alkyl halide-------> Wittig
1. PPh3 | 2. nBuLi
55
Aldehyde/ketone------> alkene
WIttig reagent

Ochem Two (1 decks)

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