Organic Chemistry Reactions 3 Flashcards

Terms Definitions
Aspartic Acid
Pyrolysis (Cracking)
H3O+ ---> Alcohols
Forming acetyl reagents
Acid Chloride
Amine ---> Amide
NaNH2 ---> Acetylide anion
Oxidation with KMnO4 (Hot)
alkene + peroxyacid
making epoxide
Catalytic Hydrogenation
(R,R)C=C(R,R)--H2/Pd/C or PtO2-->(R,R)H-C-C-H(R,R)
What is the mechanism?
Carboxylic Acid
SOCl2 ---> Acid Chloride
Whats another word for ethyne?
conc. H2SO4, heat
dehydration of alcohol
Williamson synthesis
Reactants: Alkyl halide, phenol
Products: Ether
1. CH2Cl2
2. NaOH, H2O
3. Bu4N+Br-
Basic structure of an Amino Acid
Reduction of quinone
Reactants: Quinone
Products: Phenol
1. Na2S2O4, H2O
What is the preferred synthesis method?
H2 and Pd/C OR NaBH4 ---> Amines
How is carbonation of an orgmet reagent achieved?
excess NH3
amine synthesis with alkyl halide reactant
Beckmann rearrangement
an acid-catalyzed rearrangement of an oxime to an amide
Hydrogenolysis of benzyl ethers
Reactants: Benzylic ether, H2
Products: Toluene, alcohol
1. H2, Pd
Alkyl Halide
Strong base (bulky bases are better) ---> Alkene/Alkyne @ most substituted C
How can we go from Epoxide to Alcohol?
Claisen Condensation
reaction between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone
Friedel Crafts Alkylation
Reaction conditions: R-X, AlCl3 ( lewis acid)
Making an alkene from an alcohol
Dehydration with acid
H2, Pd/C OR iron and tin reagents ---> Anilines
How do you convert an alcohol into an alkyl halide with an ester as an intermediate?
Wittig Reaction
reaction of an aldehyde or ketone with a triphenyl phosphonium ylide to give an alkene and triphenylphosphine oxide.
Making an aldehyde from a primary alcohol
Oxidation with PCC
Aromatics w/ at least 1 Benzylic Hydrogen
KMnO4 ---> benzoic acids
Can nitrogen-containing compounds be optically active?
Usually not because of nitrogen inversion but sometimes they can be isolated if the structure hinders inversion.
Aldehyde + NaBH₄ =
An aldehyde reacts with NaBH₄ to produce a primary or secondary alcohol.
Aldehyde + NaBH₄ --> 1⁰ or 2⁰ OH
Carboxylic acid reduction to 1' alcohol
Reaction condition: LiAlH4/Et2O (2) H2O/H2SO4
Which addition reactions can have carbocation rearrangement?
Hydrohalogenation and hydration, since these reactions have carbocation intermediates; halogenation, halohydrin formation, and hydroboration-oxidation don't have carbocation intermediates
2°or 3° Alkyl Halide
Any base (bulky bases are better) ---> Alkene/Alkyne @ most substituted C
What looses an H first in basic titration, the amino or carboxyl group?
The carboxyl group duh!
2⁰ OH + Na₂CrO₇ (or CrO₃/Pyridine) =
A secondary alcohol reacts with Na2CrO7 or CrO3/pyridine to produce a ketone
2⁰ OH + Na₂CrO₇ (or CrO₃/Pyridine) > Ketone
Anti-Markovnikov addition of HBr to Alkenes
Opposed to hydrohalogenation, when HBr is in the presence of ROOR anti-Markovnikov addition occurs through radical process
Making a quadruply-halogenated alkyl halide from an alkyne
Halogenation of alkyne with two equiv. X2
Things that can make an epoxide
halohydrin (intramolecular Sn2 using a base, which removes the H from the OH)
alkene (epoxidation with mCPBA or another peroxyacid)
How can you get ketones or aldehydes?
Oxidation of primary or secondary alcohols. Or ozonolysis of alkenes.
Alkyl Halide + NaCN =
An alkyl halide reacts with NaCN to produce a nitrile.
Alkyl Halide + NaCN --> Nitrile
What are the geometry and hybridization of carbon radicals?
Trigonal planar, sp2, with only one electron in the p-orbital perpendicular to the plane.
How can you think of Lithium Aluminum Hydride?
It is like an H- nucleophile.
What are some pros and cons of OsO4?
Pros: more selective
Cons: toxic and expensive. Also, sodium bisulfite (NaHSO3) is used in the hydrolysis step rather than water.
What role does tosylate usually play in reactions?
It usually acts as a good leaving group and a good protecting group.
How do you get an acetal or ketal?
When an aldehyde or ketone reacts with two equivalents of alcohol. A hemiketal or hemiacetal you get from one equivalent of alcohol.
Mechanism of conversion of 1º alcohols to alkyl halides with HX
1) The O of the OH attacks the H of HX, so the O is protonated. Now it is a good leaving group (H2O)
2) X- attacks the carbon and OH2 leaves
Mechanism of conversion of 2º and 3º alcohols to alkyl halides with HX
1) The O of the OH attacks the H of HX, so the O is protonated. Now it is a good leaving group (H2O)
2) the OH2 leaves, forming a carbocation
3) X- attacks from either side
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