Chemistry: Organic Reactions Flashcards

Terms Definitions
Serine
Glutamate Salt
Dichlorocarbene Addition
(R,R)C=C(R,R)+CHCl3--KOH-->(R,R)H-C-C(Cl2)-C-X(R,R)
Free Radical Halogenation
Amide
Hydrolysis ---> Carboxylic Acid/Amine
Reduction to make Alcohol
Combustion Reaction
Organic+0₂ --> CO₂+H₂0
What is the product?
How to Cleave an Ether!
X2, CH2Cl2
anti addition of halogen
Substitution
hydrogen replaced in saturated hydrocarbon(single)
Alkynes
H2, Lindlar catalyst ---> cis alkenes
What does acetic anydride look like?
Polymerization
chains of smaller units covalently bonded together.
What is the preferred synthesis method?
Carbonyl Compound with an α-Hydrogen
acid ---> enol
Aromatics
RCOCl, FeCl3 OR AlCl3 ---> acylated aromatic
Ester
a. RMgBr/ether b. H30+ ---> 3° Alcohol
alcohol
reaction of acetylide ion and carbonyl group gives
Grignard Reaction
addition of an organomagnesium halide toa ketone or aldehyde, to form a tertiary or secondary alcohol, respectively
Addition
adding atom(s) to double or triple bonds
What are the major and minor products?
What are epimers?
Diastereomers that differ in the configuration of ONE carbon.
H2, Lindlar's catalyst
reduction of alkynes to cis alkene
Forming Grignard Reagents
R-X + Mg in ether --RMgX
Making an aldehyde from a terminal alkyne
Hydroboration-oxidation (w/tautomerization)
Ether
HBr or HI (conc) ---> alkyl bromide or iodide/alcohol
How do Agrose gel and SDS-PAGE electrophoresis separate molecules?
Based on SIZE
Arndt-Eistert Reaction
convert a carboxylic acid to a higher carboxylic acid homologue Acid chlorides react with diazomethane to give diazoketones. In the presence of a nucleophile (water) and a metal catalyst (Ag2O), diazoketones will form the desired acid derivative
Making a doubly-halogenated alkyl halide from an alkene, creating a vicinal dihalide
Halogenation of alkene with X2
What is a cyanohydrin?
When al and ke react with HCN.
cold dilute KMnO4, or OsO4, H2O2
syn addition of di OH
Aldehyde + KMnO₄ =
An aldehyde reacts with KMnO₄ to produce a carboxylic acid.
Aldehyde + KMnO₄ --> COOH
Making an epoxide from a halohydrin
Intramolecular SN2 reaction using base
Why is a Sn2 reaction bimolecular?
Its rate-determining step is dependent on TWO species; both the substrate and the nucleophile.
Alkyl Halide + Mg/Ether =
An alkyl halide reacts with Mg/ether to produce a Grignard reagent.
Alkyl Halide + Mg/Ether --> Grignard Reagent
Ester + LiAlH₄ =
An ester reacts with LiAlH4 to produce a primary alcohol.
Ester + LiAlH₄ --> Primary Alcohol
Making an alkene from an alkyl tosylate
Beta elimination with non-nucleophilic base
Why are carboxylic acids that much more acidic?
Resonance stabilization of between the alcoholic oxygen and the carbonyl oxygen.
Carboxylate Ion + Ethyl Iodide =
A carboxylate ion reacts with ethyl iodide to produce an ester.
COO⁻ + Ethyl-I --> Ester
What's special about PCC (pyridinium chlorochromate)?
It is soluble in dichloromethane and can be used without strong acid. Other chromate oxidants are used in aqueous acid (H2SO4 + H2O). Since it is used in milder conditions, it can yield aldehydes; on more acidic conditions, the second oxidation would occur, yielding carboxylic acids.
With respect to optical activity, what do your end products of Sn1 and Sn2 reactions become?
Sn1 = racemic mixture (nucleophile can attack from either the top or the bottom of the planar carbocation), therefore loss of optical activity.
Sn2 = inversion of configuration and remains optically active.
Making an alkyl halide next to a double bond
Radical halogenation at an allylic carbon
What doesn't a nucleophile play a role in the rate of an Sn1 reaction?
It is not involved in the rate-determining step...the formation of the carbocation.
What are the best conditions for an Sn2 reaction?
You must have a strong nucleophile for the backside attack (thats what she said) with no steric hindrance.
Mechanism of dehydration of alcohols using POCl3 and pyridine
1) The oxygen of OH attacks the P of POCl3; the electrons of one of the P-Cl bonds goes to the Cl, making Cl-. The O has a positive charge.
2) pyridine, a base, picks up the H on the O, and the O-H bond electrons revert to O. Now O-POCl2 is a good leaving group.
3) Another pyridine takes away the hydrogen on a beta carbon. Its bond electrons make a pi bond between the alpha and beta carbons, and O-POCl2 leaves.
How many moles of acid are needed to neutralize 1 mole of a basic amino acid?
3 moles because of the extra R amino group.
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