Test 3

Question 1

How do you go from a keto to an enol form

Answer 1

From O to methane then methane to bond creating C bonded to alcohol, methane, and DB to CH2

Question 2

Using CH3-C(=O)-CH(CH32) make a kinetic and thermodynamic product

Answer 2

Thermodynamic product is CH3-C(=O)- negative C - (CH3)2. Kinetic product is negative CH2-C(=O)-CH(CH3)2

Question 3

What are the properties of kinetic and thermodynamic products

Answer 3

Kinetic products are formed faster and less stable while thermodynamic ones are formed over time but more stable

Question 4

What happens to a ketone when it is treated with a base (racemization)

Answer 4

Makes a racemic mix where there are up and down bonds that have enantiomers

Question 5

Draw the mechanism of the alpha halogenation of Ph-C (=O) - CH2-CH3

Answer 5

Adds two Br molecules to CH2

Question 6

Draw the mechanism of the alpha alkylation of CH(=O)-CH2CH3 with BrCH2CH3

Answer 6

Results in CH(=O)-CH (CH3)- CH2CH3

Question 7

What are the reactants used for alpha alkylation

Answer 7

LDA and THF

Question 8

What bases can be used to make a kinetic and thermodynamic product

Answer 8

Bulky bases like LDA and KOtBU are used to make a kinetic while small bases like NaOH and other NaO- compounds make a thermodynaic

Question 9

What happens as a result of a haloform reaction (Ph-C (=O)-CH3)

Answer 9

Ph-C (=O)- O- Na+ plus LG bonded to H

Question 10

What are the conditions of a haloform reaction

Answer 10

There must be a methyl bonded to the C and the other molecule can be anything but an alpha H

Question 11

What are the reactants for a claisen reaction

Answer 11

NaOR and ROH

Question 12

What is the mechanism of a claisen reaction with CH3-C(=O)-OEt with CH3-C(=O)-OEt

Answer 12

Results in CH3-C(=O)-CH2-C(=O)-OEt

Question 13

What are the reactants of a Dieckmann Condensation rxn

Answer 13

NaOR and ROH

Question 14

What is the mechanism of a Dieckmann Condensation rxn with MeO-C(=O)-(CH2)4-C(=O)-OMe

Answer 14

Results in a pentane ring with DB O on top and ester to the left (beta- ketoester)

Question 15

What causes a micheal addition rxn

Answer 15

When a Nuc attacks the beta C of an alpha-beta unsaturated ketone aldehyde or ester

Question 16

What is the mechanism of a micheal addition rxn of 2-cyclopenten-1-one and a ketone with CH2 and CH3 single bonds

Answer 16

Nuc attacks beta C, DB moves up to O. Lp on O moves down, DB attacks H+ making a 1,5- dicarbonyl compound

Question 17

What happens in a Robinson Annulation

Answer 17

Micheal rxn, aldol rxn, and aldol condensation rxn

Question 18

What is a conjugated diene

Answer 18

DB have a single bond between them

Question 19

What is a isolated diene

Answer 19

DB have two or more single bonds between them

Question 20

What is a cumulated diene

Answer 20

DBs are next to each other

Question 21

What is the mechanism of an electrophilic addition to conjugated dienes and which is the kinetic and thermodynamic product with CH2CHCHCH2

Answer 21

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)

Question 22

What are the reactants and result of a 2+2 cycloaddition

Answer 22

light causes 2 bonds to form between the two taking away the DBs