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64 Cards in this Set
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Aldehyde/ketone
NaBH4 + CH3OH |
+OH & H
primary & secondary alcohols reduces C=O only |
|
Aldehyde/ketone
1) LiAlH4 2) H2O |
+OH & H
primary and secondary alcohols strong reducing agent |
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Aldehyde/ketone
H2 Pd/C, 1 equivalent |
reduction of C=C only
creates a ketone |
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Aldehyde/ketone
H2 Pd/C excess |
reduces all pi bonds (C=O, C=C, C=N)
|
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Aldehyde/ketone: reduction of acid chloride
1) LiAH(OC(CH3)3)3 2) H2O |
milder reducing agent
stops at aldehyde stage replaces Cl with H |
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Aldehyde/ketone/ester
1) LiAH4 2) H2O |
primary alcohol
strong reducing agent reduces C=O bond +H2 & OH |
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Aldehyde/ketone
1) DIBAL-H 2) H2O |
mild reducing agent
stops at aldehyde stage +H, C=O intact |
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Aldehyde/ketone
CrO3, Na2Cr2O7, K2Cr2O7, KMnO4 |
all Cr6+ reagents except PCC oxidizes RCHO to RCOOH
carboxylic acid +OH |
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Aldehyde/ketone
Ag2O, NH4OH |
Tollen's reagent oxidizes RCHO only
primary and secondary alcohols don't react carboxylic acid +OH |
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Organolithium reagents
R-X + 2Li |
R-Li, LiX
|
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Grignard Reagents
R-X + Mg + (CH3CH2)3O |
R-Mg-X
|
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Organocuprate reagents
2 R-Li + CuI |
R2Cu- Li+ & LiI
|
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Sodium Acetylides
R-C(triple bond)C-H + Na+ & -NH2 |
R-C(triple bond)C- +Na & NH3
|
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Lithium Acetylides
R-C(triple bond)C-H + R-Li |
R-C(triple bond)C-Li + R-H
|
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Organometallic: base
R-M + H-O-R |
R-H + MO-R
R-M= RLi, RMgX, R2CuLi rxn occurs w/ H2O, ROH, RNH2, R2NH, RSH, RCOOH, RCONH2, RCONHR |
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Organometallic: aldehyde/ketone
1) RMgX or RLi 2)H2O |
+OH, R
primary, secondary, tertiary alcohols |
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Organometallic: ester
1) RMgX or RLi (2 equivalents) 2)H2O |
+OH, R
forms tertiary alcohol |
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Organometallic: acid chloride
1) RMgX or RLi 2)H2O |
+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 |
|
Organometallic: acid chloride
1) R2CuLi 2)H2O |
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 |
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Carboxylation
R-MgX + 1) CO2 2) H3O+ |
+ C=O, OH
carboxylic acid is formed |
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Protecting Alcohol
R-OH + Cl-Si(Me)2(C(CCH3)3 +base tert-butyldimethylsilyl |
R-O-TBDMS
|
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Deprotecting alcohol
R-O-TBDMS + (Bu)4 N+ -F anything in the fluoride series |
R-OH + F-TBDMS
|
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Add Cyanide
NaCN + HCL |
+OH, CN
attacks C=O |
|
Witting Reaction
P(Ph)3=C(R)2 |
Reduces C=O
Adds C=C |
|
Add primary amine
RNH2 + mild acid |
+ C=NR
reduces C=O (lost as water) |
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Add secondary amine
R2NH + mild acid |
+ C=C, NR2
reduces C=O |
|
Hydration
H2O + (H+ or OH-) cat |
+ 2OH
reduces C=O reaction has a cat. |
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Add of alcohol
ROH + H+ |
+ 2OR
reduces C=O |
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Syn of Wittig Reagent
R-CH2-X 1) P(Ph)3 2)BuLi |
(Ph)3P=CH-R
|
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Cyanohydrins to Ald/ketone
R-C(OH)(CN)(HR) |
-CN, H2O
aldehyde/ketone is formed |
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Hydroysis of Acetals
R-C(OR)2(HR) + H2O + H+cat |
-2ROH, +C=O
ketone/aldehyde formed |
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Syn Acid Chloride: form RCOOH
RCO2H + SOCl2 |
RCOCL
acid chloride is produced |
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Syn Anhydride: from RCOCl
RCOCl + -O-C=O(R) |
R-CO2-C=O
|
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Syn Anhydride: from dicarboyllic acid
(CH3(CO2H))2 + time |
cyclic anhydride
5-membered ring w/ an ester and 2 C=O |
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Syn Carboxylic Acid: from RCOCl
RCOCl + H2O + pyridine |
carboxylic acid is formed
|
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Syn Carboxylic Acid: from (RCO)2O (anhydride)
(RCO)2O + H2O |
2 carboxylic acid
|
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Syn Carboxylic Acid: from RCO2R
RCO2R + H2O + H+cat |
carboxylic acid
|
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Syn Carboxylic Acid: from RCONR2
H2O + H+cat |
carboxylic acid + R2NH+
|
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Syn ester: from RCOCl
ROH + pyridine |
RCO2R
ester is formed |
|
Syn ester: from (RCO)2O
ROH |
RCO2R
ester is formed |
|
Syn ester: from RCO2H
ROH + H2SO4 |
RCO2R
ester is formed |
|
(Ph)CH2OH + PCC or H2O excess & H+cat
|
aldehyde/ketone formed
|
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Ketone/aldehyde + H2NNH2, KOH, H2O & heat, or Zn(Hg), HCl, H2O & heat
|
C=O reduced
+ 2H |
|
Ketone/aldehyde + H2CrO4
|
primary alcohol
|
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Secondary alcohol + H2CrO4
|
ketone/aldehyde
|
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R-CH2-OH (primary alcohol) + H2CrO4
|
carboxylic acid
|
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Primary or secondary alcohol + DMSO
|
ketone/aldehyde
|
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Nomenclature
Aldehyde |
take off e and add al
if ring add carbaldehyde common names add aldehyde |
|
Nomenclature
Ketone |
drop e, add one
common name uses ketone |
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Nomenclature
Acyl (R-(C=O)-) |
either add yl or oyl
|
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Nomenclature
Enal |
molecules that have C=C, & aldehyde
add enal |
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Nomenclature
Enone |
C=C & ketone
add enone |
|
H-C=O
|
form-
common name: formic acid |
|
H3C-C=O
|
acet-
acetic acid |
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CH3-CH2-C=O
|
propion-
propionic acid |
|
CH3-CH2-CH2-C=O
|
butyr-
butyric acid |
|
CH3-CH2-CH2-CH2-C=O
|
valer-
valeric acid |
|
CH3-CH2-CH2-CH2-CH2-C=O
|
capro-
caproic acid |
|
(Ph)-C=O
|
benzo-
benzoic acid |
|
Nomenclature
carboxylic acids |
-ic
|
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Nomenclature
acyclic acid chlorides |
change -ic acid
to -yl chloride |
|
Nomenclature
cyclic acid chlorides |
change -carboxylic acid to -carbonyl chloride
|
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Nomenclature
Anhydride |
replace acid with anhydride
|
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Nomenclature
Ester |
acyl (RCO-) & alkyl group (R)
add ate |