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37 Cards in this Set

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How to synthesize R'OR?
R'O- + R-X ---> R'OR + X-
Ether
How to synthesize R'OOR?
R'OO + R-X
Etsher
How to synthesize RSH?
HS- + R-X
Thiol
How to synthesize RC(trip bond)N?
C(trip bond)N + R-X
Alkyl Cyanide
How to synthesize R=N+=N-?
N-=N+=N- + R-X
Alkyl Azide
How to synthesize R-I?
I- + R-X (X = Br, Cl)
In Acetone
Alkyl Iodide
How to synthesize an Alkane from an alkene?
Alkene + H2 -->(Pt, Pd, Rh, Ni catalyst) Alkane
Catalytic Hydrogenation
How to synthesize an anti-Markovnikov alkyl halide from an Alkene?
RHC=CH2 + HBr&ROOR ---> RH2C-CH2Br
How to synthesize an alkyl halide from an alkene?
RCH=CR2 + HX ---> RCH-CR2-X
Adds with markovnikov - H adds to C with most H's.
Addition of Hydrogen Halides
How to synthesize Alkyl HSO4 from an alkene?
RCH=CR2 + H2SO4 ---> RCH2-CR2-OSO2OH
Addition of Sulfuric Acid
Markovnikov.
How to synthesize an Alcohol from an alkene?
RCH=CR2 + H20 in acidic solution ---> CRH2-CR2-OH
Acid Catalyzed Hydration
Occurs according to Markovnikov.
How to synthesize an antimarkovnikov alcohol from an alkene?
RCH=CH2 + 1. B2H6, diglyme 2. H2O2, HO- --> RCHOH-CHR2
Hydroboration - Oxidation
Stereospecific Syn. Antimarkovnikov. Rearrangements do not occur.
How to synthesize a vicinal dihalide from an alkene?
RCH=CH2 + X2 --> XR2C-CR2X
Addition of Halogens.
Stereospecific Anti Addition
How to synthesize a vicinal halohydrin from an alkene?
(XHRC-CR'R"OH)
RCH=CH2 + Br2&H2O --> XHRC-CR'R"OH. Anti Addition. Halogen adds to C with greatest Hydrogens.
How to synthesize an Epoxide from an alkene?
RCH=CH2 + R'COOOH -> R2COCR2
How to cleave an alkene into carbonyl compunds?
RHC=CHR + 1.O3 2.Zn, H20 ---> RHC=O + RHC=O
Syn Addition is
Addition reaction in which both portions of a reagent add to the multpile bond from the same side.
Anti Addition is
Addition reaction in which the two portions of a reagent add to the multpile bond from opposite sides.
"Anti"
two substituents on adjacent atoms are 180 degrees apart.
"Gauche"
two substituents on adjacent atoms are 60 degrees apart.
"Eclipsed"
two substituents on adjacent atoms are aligned.
Tertiary & Secondary Alcohol Dehydration:
Reactants, Product, Classification
C3-COH + H2SO4& heat ---> C2C=CH2
E1 Mechanism. Rate determining step - dissociation of C3C from OH2
Primary Alcohol Dehydration:
Reactants, Product, Classification
C-COH + H2O --> C=C + H30 + H2O
E2 - H2O attachs H and C-O bond breaks in same step. Rearrangements then occur to favor most substituted double bonds.
Dehydrohalogenation of 1st, 2nd, and 3rd dregree Alkyl Halides in the presence of a strong base: Reactants, Product, Classification
H3C-CH2X + StrongBase in EtOH solvent --> H2C=CH2 + HX
Zaitsev rule: elimination favors most highly substituted double bonds.
E2 mechanism: C-H and C-X bonds broken and C=C double bond formed at same time.
In E2 Dehydrohalogenation of Alkyl Halides, which Halogen is the best leaving group? Why?
I -fastest, has weakest C-X bond. F - slowest.
Dehydrohalogenation of 2nd and 3rd dregree Alkyl Halides in the presence of a weak base: Reactants, Product, Classification
E1 Mechanism. Rate determining step - Breaking of the c-x bond to form a tertiary or secondary carbocation.
Which is more stable - trans- or cis- cycloalkenes?
Cis
Zaitsev's rule states:
beta eliminations of alcohols result in the most highly substituted alkene as the major product.
Factors governing Alkene Stability are:
1. Degree of substitution - tetrasubstituted double bonds are most stable.
2. Van der Waals (steric strain) - when large substituents are trans, more stable than cis.
How to synthesize an Alkyl Halide, given an alcohol ROH?
ROH + HX --> RX
Rank reactivity of Hydrogen halides and alcohols of varying degrees.
HI>HBr>HCl>HF.
tert>sec>prim>methyl.
How to synthesize an Alkyl Chloride, given an alcohol ROH?
ROH + SOCl2 --> RCl
How to synthesize an Alkyl Bromide using free radicals given an alkane?
RH + Br2 --> RX
Bromine will go to the tertiary carbon 80% of the time
Rank Stability of carbocations of different degrees.
Tert>sec>prim>methyl.
How do you rank in terms of polarity?
electronegativity: F>Cl>Br>I>O>C.
C-X and C-OH bonds are polar. C is the positive end.
What determines Solubility?
Low - weight alcohols (meth-eth-propanol) are soluble in water, less soluble as # c's increases. Alkyl halides are insoluble.
How to rank molecules in boiling point?
H-bonding - higher
More carbon atoms - higher