Chapter 19

Question 1

ADDN of HCN to Ketone

Answer 1

-makes cyanohydrin
-O attacks H and creates OH
-CN attacks at double bond creating an OH bond and CN bond

Question 2

Alcohol Addn (2 equivs of R-OH)

Answer 2

Starts with ketone
-Hemiacetal ( oh and OCH3 or O-r)
-Acetal (2 OCH3)

Question 3

Cyclic Acetal Formation

Answer 3

-uses a diol
-and TsOH
-c double O turns into split O cyclic

Question 4

Acetal Hydrolysis

Answer 4

-addn of H/H20 to an acetal will drive the reverse rxn
-start with acetal and get ketone

Question 5

amine addition (primary)

Answer 5

-(r-nh2)
-h2 and O on ketone bond and leave in form of water
-N-R group bones to form an imine

Question 6

Amine addition (Secondary)

Answer 6

-Same as primary expect for last step
-forms double bond in ring and amine up top
-if ketone is not symmetric multiple products can form

Question 7

Nitrile Hydrolyze

Answer 7

Uses H3O+
-forms carboxylic acid and NH3

Question 8

Aldol Rxn

Answer 8

Rxn between 2 molecules of aldehyde or Ketone
-makes a B-hydroxy Alpha aldehyde or ketone

Question 9

Aldol Condensation

Answer 9

-join 2 molecules with the loss of a small molecule
-heating results in the condensation step
-NaOH/H2o and Heat
-Gives an alpha, beta-unsaturated C–O

Question 10

Crossed Aldol

Answer 10

-Uses 2 different C–O compounds
(1 enolate, 1 Ketone)
-MESS
But can fix with different options

Question 11

Crossed aldol option 1

Answer 11

-Use one C–O with no alpha H

Question 12

Options 2 Crossed aldol

Answer 12

Use one C–O that is acidic

Question 13

Option 2 Crossed aldol

Answer 13

-Directed Aldol
- Uses LDA to form enolate of 1 C–O then slowly add 2nd C–O

Question 14

Aldol Retrosynthesis

Answer 14

-Look for alpha, beta unsaturated C–O or B-hydroxy C–O
-Makes Ketone and C–O molecule

Question 15

Intramolecular Aldol

Answer 15

-possible when two C–O are in the same chain
-forms 5 or 6 membered ring