Ch 20: Carbonyl Chem, Organometallic, RedOx Flashcards

Terms Definitions
NaBH4, CH3OH + ketone
2° Alcohol (Add H2O)
LiAlH4, H2O + ketone
2° Alcohol (Add H2O)
H2, Pd-C + ketone
2° Alcohol (Add H2O)
NaBH4, CH3OH + aldehyde
1° Alcohol (Add H2O)
H2, Pd-C + aldehyde
1° Alcohol (Add H2O)
LiAlH4, H2O + aldehyde
1° Alcohol (Add H2O)
NaBH4, CH3OH + ketone with C=C
-OH where ketone was
H2 (1 equiv), Pd-C + ketone with C=C
C=C becomes C-C only
H2 (2 equiv), Pd-C + ketone with C=C
C=C becomes C-C, ketone becomes -OH
RCOCL + LiAlH4, H2O
1° Alcohol
RCOCL + LiAlH[OC(CH3)3]3 , H2O
Aldehyde (mild, stops early)
R-COOR' + LiAlH4, H2O
1° Alcohol
R-COOR' + DIBAL-H, H2O
Aldehyde (mild, stops early)
R-COOH + LiAlH4, H2O
1° Alcohol
RCON (2 sticks on N) + LiAlH4, H2o
RCH2-N (2 sticks on N)
Aldehyde + O3
RCOOH (carboxylic acid)
Aldehyde + AG2O, NH4OH
RCOOH (carboxylic acid)
R-X + 2 Li
R-Li + LiX
R-X + Mg, (CH3CH2)2O
R-Mg-X
2 R-Li + CuI
R2Cu- Li+ + LiI
R-C≡C-H + Na+ NH2-
R-C≡C- Na+ (Sodium acetylide) + NH3
R-C≡C-H + R'-Li
R-C≡C-Li (lithium acetylide) + R'-H
Aldehyde + R"MgX or R"Li, H2O
carbonyl to -OH, R" added at bottom
Ketone + R"MgX or R"Li, H2O
carbonyl to -OH R" added at bottom
RCOOR' + R"MgX or R"Li, H2O
3° Alcohol
RCOCl + R"MgX or R"Li (2 equiv), H2O
3° Alcohol
RCOCl + R'2CuLi, H2O
ketone w/ R'
R-MgX + CO2, H3O+
RCOOH
epoxide + RLi, RMgX, or R2CuLi (all w/ H2O)
open epoxide with R and O become -OH
How to protect an alcohol?
1] R-O-H + Cl-TBDMS + imidazole --> R-O-TBDMS
2] R-O-TBDMS + (CH3CH2CH2CH2)4N+F- -->R-O-H + F-TBDMS
review a,b-unsaturated aldehydes and ketones
y
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