Test 3 Flashcards
(22 cards)
How do you go from a keto to an enol form
From O to methane then methane to bond creating C bonded to alcohol, methane, and DB to CH2
Using CH3-C(=O)-CH(CH32) make a kinetic and thermodynamic product
Thermodynamic product is CH3-C(=O)- negative C - (CH3)2. Kinetic product is negative CH2-C(=O)-CH(CH3)2
What are the properties of kinetic and thermodynamic products
Kinetic products are formed faster and less stable while thermodynamic ones are formed over time but more stable
What happens to a ketone when it is treated with a base (racemization)
Makes a racemic mix where there are up and down bonds that have enantiomers
Draw the mechanism of the alpha halogenation of Ph-C (=O) - CH2-CH3
Adds two Br molecules to CH2
Draw the mechanism of the alpha alkylation of CH(=O)-CH2CH3 with BrCH2CH3
Results in CH(=O)-CH (CH3)- CH2CH3
What are the reactants used for alpha alkylation
LDA and THF
What bases can be used to make a kinetic and thermodynamic product
Bulky bases like LDA and KOtBU are used to make a kinetic while small bases like NaOH and other NaO- compounds make a thermodynaic
What happens as a result of a haloform reaction (Ph-C (=O)-CH3)
Ph-C (=O)- O- Na+ plus LG bonded to H
What are the conditions of a haloform reaction
There must be a methyl bonded to the C and the other molecule can be anything but an alpha H
What are the reactants for a claisen reaction
NaOR and ROH
What is the mechanism of a claisen reaction with CH3-C(=O)-OEt with CH3-C(=O)-OEt
Results in CH3-C(=O)-CH2-C(=O)-OEt
What are the reactants of a Dieckmann Condensation rxn
NaOR and ROH
What is the mechanism of a Dieckmann Condensation rxn with MeO-C(=O)-(CH2)4-C(=O)-OMe
Results in a pentane ring with DB O on top and ester to the left (beta- ketoester)
What causes a micheal addition rxn
When a Nuc attacks the beta C of an alpha-beta unsaturated ketone aldehyde or ester
What is the mechanism of a micheal addition rxn of 2-cyclopenten-1-one and a ketone with CH2 and CH3 single bonds
Nuc attacks beta C, DB moves up to O. Lp on O moves down, DB attacks H+ making a 1,5- dicarbonyl compound
What happens in a Robinson Annulation
Micheal rxn, aldol rxn, and aldol condensation rxn
What is a conjugated diene
DB have a single bond between them
What is a isolated diene
DB have two or more single bonds between them
What is a cumulated diene
DBs are next to each other
What is the mechanism of an electrophilic addition to conjugated dienes and which is the kinetic and thermodynamic product with CH2CHCHCH2
DB attacks H onto Br, Br attacks positive charge making 1,2 addition product (kinetic) but intermediate has resonance where the positive charge moves to the far right creating a 1,4 addition product when Br attacks (thermodynamic)
What are the reactants and result of a 2+2 cycloaddition
light causes 2 bonds to form between the two taking away the DBs
