Organic Chemistry Final
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- How to synthesize R'OR?
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R'O- + R-X ---> R'OR + X-
Ether - How to synthesize R'OOR?
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R'OO + R-X
Etsher - How to synthesize RSH?
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HS- + R-X
Thiol - How to synthesize RC(trip bond)N?
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C(trip bond)N + R-X
Alkyl Cyanide - How to synthesize R=N+=N-?
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N-=N+=N- + R-X
Alkyl Azide - How to synthesize R-I?
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I- + R-X (X = Br, Cl)
In Acetone
Alkyl Iodide - How to synthesize an Alkane from an alkene?
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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?
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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?
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RCH=CR2 + H2SO4 ---> RCH2-CR2-OSO2OH
Addition of Sulfuric Acid
Markovnikov. - How to synthesize an Alcohol from an alkene?
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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?
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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?
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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.
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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
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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:
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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.
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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?
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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?
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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?
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H-bonding - higher
More carbon atoms - higher