Carbonyls

Question 1

Cyano hydrin formation

Answer 1

NaCN and water

reversible and produces OH-

Question 2

+ NaBH4

Answer 2

reduces carbonyls in alcohol with BH4-

Gives BH3 and ROH and RO-

Question 3

+ LiAlH4

Answer 3

Reduces carbonyls in Et2O
Then hydrolysis
forms Al(OR)4 which reacts with water

Question 4

organo lithium synthesis

Answer 4

haloalkane + Li in THF

gives LiR and LiX

Question 5

Grignard reagent synthesis

Answer 5

Mg + haloalkane in Et2O

Question 6

organometallic + carbonyl

Answer 6

produces alcohol after hydrolysis

have electrophilic carbons

Question 7

+ water pH7

Answer 7

to hydrate C(OH)2R2

h2o H abstraction by H2O

Question 8

+ alcohol pH7

Answer 8

to hemiacetal

Question 9

addition at pH<7

Answer 9

forms more electrophilic species by addition of H+

Question 10

addition at pH>7

Answer 10

forms more nucleophilic species by deprotonation

Question 11

Carbon elecrtophelicity

Answer 11

more delocalisation, weaker C=O, lower dipole

Question 12

acyl chloride + alcohol

Answer 12

ester

Question 13

anhydride +alcohol

Answer 13

ester + carboxylate

Question 14

carbonyl + pyridine

Answer 14

to ester via pyridine containing carbonyl intermediate

also abstracts proton

Question 15

alcohol + carboxylic acid

Answer 15

to ester and water
acid catalysed is reversible
base catalysed consumes OH to carboxylate- irreversible

Question 16

acyl chloride + amine

Answer 16

amine + HCl

Question 17

schotten-baumann amide synthesis

Answer 17

aryl acyl chloride and Me2-NH-Me2

in CH2Cl2 NaOH and water

Question 18

acyl chlorides from carboxylic acids

Answer 18

SOCl2 to acyl chloride SO2 and HCl

Question 19

enol to ketone

Answer 19

tautomerism

acid or base catalysed

Question 20

stereochemistry and enolates

Answer 20

enolisation destroys carbonyl adjacent stereocentres

Question 21

alpha position mono functionalisation

Answer 21

halogenation
by acid catalysis via enol
by base catalysis to carboxylate and CHX3. Nucelophilic to basic attack

Question 22

symmetric c-c bond formation

aldol

Answer 22

alpha carbon and carbonyl carbon
water elimination from product
acid or base catalysed

Question 23

ketone from acid derivative

Answer 23

acyl chloride + Me-NH-OMe with RMgBr
MgBr+ adds to intermediate stabilising it
acid workup collapse

Question 24

acetal formation scheme

Answer 24

carbonyl equilibrates hemiacetal equilibrates acetal

using tosic acid

Question 25

aldehyde/ketone and primary amine

Answer 25

to imine R-C(NR)-R | optimum pH

Question 26

oxime

Answer 26

R-C(NOH)-R | acid hydrolysis to carbonyl

Question 27

aldehyde/ketone + secondary amine

Answer 27

enamine | alpha carbon's hydrogen attacked

Question 28

ylid generation

Answer 28

PPh3 + RX + base

Question 29

carbonyls to alkene

Answer 29

ylid | to alkene and O=PPh3

Question 30

gradual reduction

Answer 30

carboxylic to aldehyde with DIABL | aldehyde to alcohol with NaBH4

Question 31

Jones Oxidation

Answer 31

dichromate and dilute H2SO4 in acetone

Question 32

H+ sensitive oxidation

Answer 32

PCC stops at aldehyde

Question 33

ketones to esters

Answer 33

peracids + carboxylic

Question 34

crossed aldol | assymetric c-c bond formation

Answer 34

only enolise one carbonyl other more electrophilic

Question 35

diketone from ester

Answer 35

base catalysed deprotonation of prodict so irreversible NaOEt

Question 36

conjugate enolate additon

Answer 36

to an alpha beta unsaturated carbonyl | is thermodynamic product over more hindered aldol

Question 37

Ring formation

Answer 37

conjugate additon then intramolecular aldol then dehydration alpha beta unsaturated + diketone +NaOEt