CH. 19

Question 1

What is the product of the following reaction?

Answer 1

ketone –> alkene

Question 2

What is the product of the following reaction?

Answer 2

catalytic hydrogenation

ketone or aldehyde –> alcohol

Question 3

What is the product of the following reaction?

Answer 3

Oxidation

Primary alcohol –> carboxylic acid

Question 4

What is the product of the following reaction?

Answer 4

Oxidation

Secondary alcohol –> ketone

Question 5

What is the product of the following reaction?

Answer 5

Oxidation

secondary alcohol –> ketone

Question 6

What is the product of the following reaction?

Answer 6

Oxidation

primary alcohol –> aldehyde

Question 7

What is the product of the following reaction?

Answer 7

Clemmenson Reduction

ketone or aldehyde –> alkane

Question 8

What is the product of the following reaction?

Answer 8

Raney-Nickel Reduction

ketone or aldehyde –> alkane

Question 9

What is the product of the following reaction?

Answer 9

Catalytic Hydrogenation

alkene –> alkane

ALWAYS SYN ADDN

Question 10

What is the product of the following reaction?

Answer 10

Catalytic Hydrogenation; poisoned catalyst

Alkyne –> cis-alkene

Question 11

what is an oxidation reaction

Answer 11

losing electrons, carbon losing bonds to less electronegative atoms, and gaining bonds with more electroneg atoms

gaining O, O₂

losing H₂

Question 12

what is a reduction reaction

Answer 12

Carbon gaining bonds to less electroneg atoms and losing bonds to more electroneg atoms

gaining H₂

losing O, O₂

Question 13

What is the product of the following reaction?

Answer 13

Suzuki Coupling

Question 14

What is the product of the following reaction?

Answer 14

Heck Coupling

Question 15

What is the product of the following reaction?

Answer 15

Alkene Metathesis Cross

Question 16

What is the product of the following reaction?

Answer 16

Alkene Metathesis Ring Closing

Question 17

What is the name of this functional group?

Answer 17

an Imine

Question 18

What is the name of this functional group?

Answer 18

Hydrazone

Question 19

What is the name of this functional group?

Answer 19

Oxime

Question 20

What reagents can you use for reductive amination?

Answer 20

NaBH₄

or

NaBH₃CN

Question 21

What is the name of this aldol condensation product?

Answer 21

Question 22

What is the name of the mechanism that is the only acception for OH as a leaving group?

Answer 22

E1cb

Question 23

does low heat favor the beta-hydroxy aldehyde compound in aldol condensations or the alpha-beta-unsaturated aldehyde?

Answer 23

low heat favors the beta-hydroxy aldehyde compound

Question 24

does heat favor the beta-hydroxy aldehyde compound in aldol condensations or the alpha-beta-unsaturated aldehyde?

Answer 24

heat favors the alpha-beta-unsaturated aldehyde

Question 25

What is the name of this aldol condensation product?

Answer 25

Question 26

How do you improve selectivity of crossed aldol reactions?

Answer 26

use a very strong base (ex: LDA)

or

no alpha H’s present

Question 27

Is this aldol condensation kinetic or thermodynamic?

Answer 27

thermodynamic

the proton transfer is reversible

Question 28

Is this aldol condensation kinetic or thermodynamic?

Answer 28

kinetic

proton transfer not reversible

Question 29

where on this molecule does NaOH favor deprotonation?

Answer 29

Question 30

where on this molecule does LDA favor deprotonation?

Answer 30

Question 31

What type of rings is an intramoleular aldol reaction successful for?

Why are other rings not favorable?

Answer 31

5 or 6 membered rings are successful

other rings not successfull due to relative instability

Question 32

for this starting material in a intramolecular aldol reactions, which site is preferred to act as the electrophile?

Which site is preferred to act as the enolate?

Answer 32