functional group interconversions

Question 1

What is a hydrate and how is is made?

Answer 1

Addition of water to an aldehyde or ketone to give a di-hydroxyl product. The reaction is in equilibrium

Question 2

Jones reagent and their use

Answer 2

Oxidation of a primary alcohol to a carboxylic acid or secondary alcohol to a ketone. CrO3, H2SO4, H2O

Question 3

Oxidation of a primary alcohol to an aldehyde ONLY with mechanism

Answer 3

Pyridinium dichromate (PDC). Notes for mechanism

Question 4

What will LiAlH4 reduce

Answer 4

Ketones, aldehydes and esters to primary alcohols, tosylates and alkyl bromides to alkanes, nitriles to amines, amide to amines

Question 5

Mechanism for the reductionof an amide using LiAlH4

Answer 5

Check notes

Question 6

Reductions using NaBH4

Answer 6

Does not reduce amides, esters or alkyl halides. Will reduce ketones and aldehydes to alcohols

Question 7

Reduction of enones

Answer 7

Uses NaBH4 and either CeCl3 or CuI, MeOH. CeCl3 gives the 1,2 unsaturated alcohol. CuI and MeOH gives an alcohol product

Question 8

Enone + NaBH4, CuI and MeOH reaction scheme

Answer 8

See notes

Question 9

Ester to aldehyde reagent

Answer 9

DIBALH at -70 degrees

Question 10

Draw the structure of DIBALH

Answer 10

Notes

Question 11

Cyanide to aldehyde

Answer 11

DIBALH at -70 degrees

Question 12

Alkyl halide to grignard reagent

Answer 12

addition of DRY Mg ether. This Mg ether must be dry

Question 13

Amines from alcohols. Reaction name and reagents

Answer 13

Reductive amination. PDC to oxidise the alcohol to a ketone. Amine, NaCNBH3 to reduce the ketone to an amine

Question 14

Intermediate of reductive amination

Answer 14

Iminium ion

Question 15

Amines from tosylates or alkyl halides using azides

Answer 15

NaN3 to give an azide, the H2, Pd to give the amines

Question 17

Protection and deprotection of alcohols using tert-butyldimethylsilyl

Answer 17

Protection = TBDMSCI, imidazole
Deprotection = TBAF

Question 18

What is TBAF

Answer 18

Bu4NF

Question 19

What is imidazole

Answer 19

Structure is in notes. 5 membered ring with two nitrogen species and very very weak base

Question 20

Other uses of TBDMSCI

Answer 20

Is a very bulky substituent and so can hinder the formation of a product if two can form

Question 21

Oxidation of a secondary alcohol to a ketone

Answer 21

CrO3,H2SO4, H2O

Question 22

Carboxylic acid to ester

Answer 22

SOCl2 Et3N, ROH

Question 23

Carboxylic acid to amide

Answer 23

SOCl2 EtN3, NH3

Question 24

2nd or 3rd amine to primary amine

Answer 24

Hydrogenolysis
H2, Pd/C

Question 25

Ester to alkyl

Answer 25

H3O+, HCl/heat
acid hydrolysis then decarboxylation

Question 26

Alkene to epoxide

Answer 26

mCPBA

Question 27

Alcohol to tosylate

Answer 27

TsCl, pyridine

Question 28

Lactone to diol

Answer 28

LiAlH4

Question 29

what is Lactone

Answer 29

cyclic carboxylic esters