chp 17

Question 1

Oxidation a primary alcohol
reagents :
product:

Answer 1

Oxidating a primary alcohol
reagents : PCC Ch2Cl4
product: aldehyde

Question 2

Oxidation of a secondary alcohol
reagents :
products :

Answer 2

Oxidation of a secondary alcohol
reagents : PCC CH2Cl4 or Jones H2SO4
products : ketone

Question 3

ozonolysis of Alkenes lead to ketones or aldehydes

reagents:

Answer 3

ozonolysis of Alkenes lead to ketones or aldehydes

reagents: O3, (Ch3)2S

Question 4

alkyne to aldehyde

Answer 4

antimarkovnikov addition of OH then goes through tautoumerization

1) BH3, THF
2) H2O2, H20, NaOH

Question 5

alkyne to ketone

Answer 5

markovnikov addition of OH and goes through tautermerization

1) H20
2) H2So4

Question 6

FC acylation to ketones to aldehyde

Answer 6

benzene + RCOCL, alcl3

h30+

Question 7

Reduction of aldehyde or ketone

Answer 7

C=O to OH
NaBH4, C2H5OH

or selective for not reducing c=c
LiAlH4, batman, H3O+

Question 8

hemiketal synthesis

vs ketal synthesis

Answer 8

hemiKetal R,R, OH, OR
ketone + ROH, H+, heat

ketal R,R,OR,OR
ketone + ROH (excess), H+, Heat

Question 9

hemiacetal vs acetal synthesis

Answer 9

hemiacetal R,H,OH,OR
aldehyde +ROH, H+,

Acetal R,H,RO,OR
aldehyde + ROH (excess) H+, heat

Question 10

geminal diol synthesis

Answer 10

ketone or aldehyde + h20

not stable

Question 11

cyclic acetal for protection

Answer 11

C=O is protected by OH OH

OH OH H+ and Heat

remove protection with H3O+ and heat

Question 12

imine synthesis

Answer 12

primary amine + carboxylic acid

amine attacks c=o

makes c=n

Question 13

enamine synthesis

Answer 13

secondary amine + carboxylic acid

make C-N and a double bond between a carbon where C=O was

Question 14

oximes

Answer 14

hydroxyl amine + carbonyl

Question 15

hydrazone

Answer 15

hydrazine + carbonyls

Question 16

wittig : carbonyl to alkene

Answer 16

Ylide formation
CH3-BR + Ph3P

wittig
carbonyl + ylide

Question 17

clemenson reduction

Answer 17

Zn(Hg)

HCl, H2O, heat