organic 5

Question 1

a higher pka meansss

Answer 1

a weaker acid
a stronger bonded H,, a stable H

Question 2

pka of alpha H’s in the double ester type thing

Answer 2

10-11

Question 3

pka of aldehyde alpha H

Answer 3

5-13

Question 4

pka of ketone H

Answer 4

20

Question 5

pka of ester H’s

Answer 5

25

Question 6

whats needed to make an ester enolate

Answer 6

a strong base: LDA

or LDA, Me3SiCl and TiCl4

Question 7

ester + LDA then aldehyde

Answer 7

Lithium enolate
C=C-O-Li

O-Li lone pair attacks the C of carbonyl,, makes O-

protonates and then done

Question 8

ester + LDA + Me3SiCl + TiCl4 + aldehyde

Answer 8

makes silyl enol ether
c=c-o-si-Me3 // c=c-o-TMs

add TiCl4

forms OH and carbonyl.

Question 9

ester + NaOEt

Answer 9

enolate

Question 10

ester + LDA

Answer 10

lithium enolate

Question 11

getting rid of a carbonyl and forming a double bond - whole reaction

Answer 11

make an enclave,, attack a carbonyll,, form a O-
protonate it OH

remove a H,, make O- and a double bond,, protonate the Oh

use the O- and double bond to form another double bond and the H2O

Question 12

2 ethyl acetates to give a long chain,, one ester and one ketone end

Answer 12

enolisation,, attack the other ethyl acetate,, form O-
use this to remove the ester group and leave the other group there.

Question 13

when looking at reactants and products what must we think of

Answer 13

• has a ring been made ?
• has a new bond been made?

these would need an enolate to be formed so it can bond to other things

• same amount of carbons?
  intramolecular mechanism ( reacting with itself)
• has anything been taken away // added?
  see how u could have added // removed stuff,, use of double bond and O- or O- and kick off

Question 14

what can u do with an O-

Answer 14

u can form a C=O and kick off another group

Question 15

amount of rings that we like and that are stable

Answer 15

5/6 ringsssss