Organic Chemistry Reagents Flashcards

Terms Definitions
HX --> ether (addition on alkene)
Markovnikov addition
X2 --> CH2Cl2 (addition on alkene)
Anti addition
X2 --> H2O (addition on alkene)
Markovnikov, syn addition of halohydrin
Hg(OAc)2, H2O/THF --> NaBH4 (addition on alkene)
Markovnikov, anti addition of water
BH3, THF --> H2O2, OH- (addition on alkene)
Non-Markovnikov, syn addition of water (hydroboration & oxidation)
CHCl3, KOH --> (addition on alkene)
Dichlorocarbene addition at double bond
CH2I2, Zn(Cu) --> Ether (addition on alkene)
Simmons-Smith addition of carbene
H2 --> Pd/C or PtO2 (addition on alkene)
Catalytic hydrogenation with syn addition
1. OsO4 --> 2. NaHSO3, H2O or OsO4, NMO (addition on alkene)
Hydroxylation with OsO4 with syn addition
1. O3 --> 2. Zn/H3O+ (alkene cleavage)
Double bond becomes C=O
NaNH2 --> RCH2Br --> (alkylation of alkyne)
Terminal alkyne followed by an internal alkyne
HX --> ether (addition on alkyne)
Markovnikov addition (Halogens add to same carbon & H's add to same carbon)
X2 --> CH2Cl2 (addition on alkyne)
2 halogens add to each carbon of the triple bond
H2SO4, H2O --> HgSO4 (addition on alkyne)
A terminal, methyl ketone forms
BH3 --> H2O2 (addition on alkyne)
Hydroboration/Oxymercuration forms an aldehyde
2 H2 --> Pd/C (alkyne reduction)
alkane product
H2 --> Lindlar catalyst (alkyne reduction)
Cis alkene
Li --> NH3 (alkyne reduction)
Trans alkene
NBS --> CCl4 (preparation of alkyl halides)
Bromine adds in the allylic position
HX --> Ether (preparation of alkyl halides)
X replaces the alcohol
SOCl2 --> Pyridine (preparation of alkyl halides)
Cl replaces the alcohol
PBr3 --> Ether (preparation of alkyl halides)
Br replaces the alcohol
Mg --> Ether (alkyl halide reaction)
Mg forms between R and X
2 Li --> Pentane (alkyl halide reaction)
Li replaces X on the carbon chain and forms LiX as well
SN1 reaction
only occurs with secondary and tertiary alkyl halides and forms an intermediate carbocation. only polar, protic solvents work (water, alcohols, and H2O alcohol mixtures). Nucleophile has NO effect on rate of reaction. More substituted substrate is best.
SN2 reaction
Highly favored in primary reactions, competes with E2 with secondary reactions, and does not occur with tertiary reactions. Polar, aprotic solvents work best (HMPA, CH3CN, DMF, DMSO). Basic, negative nucleophiles are best.
E1 reaction
only occurs with secondary and teritary alkyl halides and forms an intermediate carbocation. only polar, aprotic solvents work (water, alcohols, and H2O alcohol mixtures). Occurs in nonbasic solutions
E2 reaction
occurs with primary & secondary alkyl halides with strong bulky bases, and more favored than SN2 with secondary substrates. Favored with tertiary substrates (strong bases).
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