Ochem Test 3

Front 1

Aldehyde/ketone
NaBH4 + CH3OH

Back 1

+OH & H
primary & secondary alcohols
reduces C=O only

Front 2

Aldehyde/ketone
1) LiAlH4 2) H2O

Back 2

+OH & H
primary and secondary alcohols
strong reducing agent

Front 3

Aldehyde/ketone
H2 Pd/C, 1 equivalent

Back 3

reduction of C=C only
creates a ketone

Front 4

Aldehyde/ketone
H2 Pd/C excess

Back 4

reduces all pi bonds (C=O, C=C, C=N)

Front 5

Aldehyde/ketone: reduction of acid chloride
1) LiAH(OC(CH3)3)3
2) H2O

Back 5

milder reducing agent
stops at aldehyde stage
replaces Cl with H

Front 6

Aldehyde/ketone/ester
1) LiAH4
2) H2O

Back 6

primary alcohol
strong reducing agent
reduces C=O bond
+H2 & OH

Front 7

Aldehyde/ketone
1) DIBAL-H
2) H2O

Back 7

mild reducing agent
stops at aldehyde stage
+H, C=O intact

Front 8

Aldehyde/ketone
CrO3, Na2Cr2O7, K2Cr2O7, KMnO4

Back 8

all Cr6+ reagents except PCC oxidizes RCHO to RCOOH
carboxylic acid
+OH

Front 9

Aldehyde/ketone
Ag2O, NH4OH

Back 9

Tollen's reagent oxidizes RCHO only
primary and secondary alcohols don't react
carboxylic acid
+OH

Front 10

Organolithium reagents
R-X + 2Li

Back 10

R-Li, LiX

Front 11

Grignard Reagents
R-X + Mg + (CH3CH2)3O

Back 11

R-Mg-X

Front 12

Organocuprate reagents
2 R-Li + CuI

Back 12

R2Cu- Li+ & LiI

Front 13

Sodium Acetylides
R-C(triple bond)C-H + Na+ & -NH2

Back 13

R-C(triple bond)C- +Na & NH3

Front 14

Lithium Acetylides
R-C(triple bond)C-H + R-Li

Back 14

R-C(triple bond)C-Li + R-H

Front 15

Organometallic: base
R-M + H-O-R

Back 15

R-H + MO-R
R-M= RLi, RMgX, R2CuLi
rxn occurs w/ H2O, ROH, RNH2, R2NH, RSH, RCOOH, RCONH2, RCONHR

Front 16

Organometallic: aldehyde/ketone
1) RMgX or RLi
2)H2O

Back 16

+OH, R
primary, secondary, tertiary alcohols

Front 17

Organometallic: ester
1) RMgX or RLi (2 equivalents)
2)H2O

Back 17

+OH, R
forms tertiary alcohol

Front 18

Organometallic: acid chloride
1) RMgX or RLi
2)H2O

Back 18

+OH
reduces only C=O
add 1,2 addition form alpha C
more reactive organometallic regents (RMgX or RLi) add two equivalents of R to an acid chloride to form a tertiary alcohol

Front 19

Organometallic: acid chloride
1) R2CuLi
2)H2O

Back 19

C=O intact, +R-group
ketone is formed
add 1,4 addition from alpha C
reduces C=C
less reactive organometallic reagents (R2CuLi) add only one equivalent of R to an acid chloride

Front 20

Carboxylation
R-MgX + 1) CO2 2) H3O+

Back 20

+ C=O, OH
carboxylic acid is formed

Front 21

Protecting Alcohol
R-OH + Cl-Si(Me)2(C(CCH3)3 +base
tert-butyldimethylsilyl

Back 21

R-O-TBDMS

Front 22

Deprotecting alcohol
R-O-TBDMS + (Bu)4 N+ -F
anything in the fluoride series

Back 22

R-OH + F-TBDMS

Front 23

Add Cyanide
NaCN + HCL

Back 23

+OH, CN
attacks C=O

Front 24

Witting Reaction
P(Ph)3=C(R)2

Back 24

Reduces C=O
Adds C=C

Front 25

Add primary amine
RNH2 + mild acid

Back 25

+ C=NR
reduces C=O (lost as water)

Front 26

Add secondary amine
R2NH + mild acid

Back 26

+ C=C, NR2
reduces C=O

Front 27

Hydration
H2O + (H+ or OH-) cat

Back 27

+ 2OH
reduces C=O
reaction has a cat.

Front 28

Add of alcohol
ROH + H+

Back 28

+ 2OR
reduces C=O

Front 29

Syn of Wittig Reagent
R-CH2-X
1) P(Ph)3
2)BuLi

Back 29

(Ph)3P=CH-R

Front 30

Cyanohydrins to Ald/ketone
R-C(OH)(CN)(HR)

Back 30

-CN, H2O
aldehyde/ketone is formed

Front 31

Hydroysis of Acetals
R-C(OR)2(HR) + H2O + H+cat

Back 31

-2ROH, +C=O
ketone/aldehyde formed

Front 32

Syn Acid Chloride: form RCOOH
RCO2H + SOCl2

Back 32

RCOCL
acid chloride is produced

Front 33

Syn Anhydride: from RCOCl
RCOCl + -O-C=O(R)

Back 33

R-CO2-C=O

Front 34

Syn Anhydride: from dicarboyllic acid
(CH3(CO2H))2 + time

Back 34

cyclic anhydride
5-membered ring w/ an ester and 2 C=O

Front 35

Syn Carboxylic Acid: from RCOCl
RCOCl + H2O + pyridine

Back 35

carboxylic acid is formed

Front 36

Syn Carboxylic Acid: from (RCO)2O (anhydride)
(RCO)2O + H2O

Back 36

2 carboxylic acid

Front 37

Syn Carboxylic Acid: from RCO2R
RCO2R + H2O + H+cat

Back 37

carboxylic acid

Front 38

Syn Carboxylic Acid: from RCONR2
H2O + H+cat

Back 38

carboxylic acid + R2NH+

Front 39

Syn ester: from RCOCl
ROH + pyridine

Back 39

RCO2R
ester is formed

Front 40

Syn ester: from (RCO)2O
ROH

Back 40

RCO2R
ester is formed

Front 41

Syn ester: from RCO2H
ROH + H2SO4

Back 41

RCO2R
ester is formed

Front 42

(Ph)CH2OH + PCC or H2O excess & H+cat

Back 42

aldehyde/ketone formed

Front 43

Ketone/aldehyde + H2NNH2, KOH, H2O & heat, or Zn(Hg), HCl, H2O & heat

Back 43

C=O reduced
+ 2H

Front 44

Ketone/aldehyde + H2CrO4

Back 44

primary alcohol

Front 45

Secondary alcohol + H2CrO4

Back 45

ketone/aldehyde

Front 46

R-CH2-OH (primary alcohol) + H2CrO4

Back 46

carboxylic acid

Front 47

Primary or secondary alcohol + DMSO

Back 47

ketone/aldehyde

Front 48

Nomenclature
Aldehyde

Back 48

take off e and add al
if ring add carbaldehyde
common names add aldehyde

Front 49

Nomenclature
Ketone

Back 49

drop e, add one
common name uses ketone

Front 50

Nomenclature
Acyl (R-(C=O)-)

Back 50

either add yl or oyl

Front 51

Nomenclature
Enal

Back 51

molecules that have C=C, & aldehyde
add enal

Front 52

Nomenclature
Enone

Back 52

C=C & ketone
add enone

Front 53

H-C=O

Back 53

form-
common name: formic acid

Front 54

H3C-C=O

Back 54

acet-
acetic acid

Front 55

CH3-CH2-C=O

Back 55

propion-
propionic acid

Front 56

CH3-CH2-CH2-C=O

Back 56

butyr-
butyric acid

Front 57

CH3-CH2-CH2-CH2-C=O

Back 57

valer-
valeric acid

Front 58

CH3-CH2-CH2-CH2-CH2-C=O

Back 58

capro-
caproic acid

Front 59

(Ph)-C=O

Back 59

benzo-
benzoic acid

Front 60

Nomenclature
carboxylic acids

Back 60

-ic

Front 61

Nomenclature
acyclic acid chlorides

Back 61

change -ic acid
to -yl chloride

Front 62

Nomenclature
cyclic acid chlorides

Back 62

change -carboxylic acid to -carbonyl chloride

Front 63

Nomenclature
Anhydride

Back 63

replace acid with anhydride

Front 64

Nomenclature
Ester

Back 64

acyl (RCO-) & alkyl group (R)
add ate