Handout 2 Material

Question 1

What is the reactivity series of functional groups

Answer 1

Iminium ion, aldehyde, acid chloride, ketone, minimum ion, ketone, mine, epoxide, ester, carboxylic acid, nitrile, amide

Question 2

Why do we use weakest reducing agent for functional group?

Answer 2

To avoid side reactions

Question 3

What is reactivity series of reducing agents starting with the weakest?

Answer 3

LiAlH4, DIBAL-H, BH3.THF, LiBH4, NaBH4, LiAlH(OBut)3, NaBH3CN

Question 4

What is special about the BHTF mechanism?

Answer 4

Form borate ester which goes on to react further

Question 5

What happens when you reduce ester with LiALH4?

Answer 5

You get primary alcohol

Question 6

What are some common oxidising agents?

Answer 6

potassium dichromate, potassium permanganate, Jones reagent

Question 7

What is a common oxidising agent for secondary alcohol to ketone?

Answer 7

PCC

Question 8

How do you convert primary alcohol to aldehyde?

Answer 8

Swern oxidation

Question 9

What process happens in Wolf Kischner and what is the reagent?

Answer 9

H2NNH2 and ketone to corresponding alkane

Question 10

What process happens in Bayer-Villiger reaction and what process happens?

Answer 10

ketone to ester using MCPBA

Question 11

What are the products of the Swern oxidation?

Answer 11

Me2S and aldehyde

Question 12

What are the reagents in the Clemmenson reaction?

Answer 12

zinc mercury amalgam and HCl

Question 13

What is the pattern for migratory aptitude in the Bayer Villiger reaction?

Answer 13

Carbocation stability

Question 14

What happens to stereochemistry in Bayer-Villiger reaction?

Answer 14

Retention of stereochemistry

Question 15

How do you convert carboxylic acid to acid chloride?

Answer 15

Thionyl chloride or PCl5

Question 16

What happens when you react a carboxylic acid with base?

Answer 16

An Sn2 can occur

Question 17

What is the product of carboxylic acid and diazomethane?

Answer 17

ester and nitrogen gas

Question 18

How can you convert an acid chloride to an amide?

Answer 18

reaction of amine and acid chloride

Question 19

What is an advantage of DCC coupling and what is the process?

Answer 19

avoids racemisation of chiral centres in amide formation and it converts carboxylic acid to amide by reaction with DCC

Question 20

Does DMAP or DCC react faster with a nucleophile?

Answer 20

DMAP

Question 21

How do you reduce an amide to nitrile?

Answer 21

thionyl chloride

Question 22

How do you convert nitrile to carboxylic acid?

Answer 22

acid/H20 and heat

Question 23

What is the product of an amine reduction using LiAlH4?

Answer 23

amine

Question 24

What happens when you react a nitrile with DIBAL-H?

Answer 24

You get aluminium complex. If excess used reacts again otherwise breaks down in presence of acid and water to imine then carboxylic acid.

Question 25

What are the reagents for reductive amination?

Answer 25

NaBH(OAc)3 or NaBH3CN

Question 26

What is the process of reductive amination?

Answer 26

tertiary amine from carboxylic acid and amine via amine

Question 27

What are reagents in Appell reaction and what is the process?

Answer 27

primary alcohol to alkyl halide. PPh3 and CCl4 (or other tetrahalide)

Question 28

What are some other methods to make alkyl halides?

Answer 28

Tosylates then Sn2 | Use SoCl2 or PBr3 also Sn2 like reaction

Question 29

What are the reagents for Mitsunubu reaction?

Answer 29

"DEAD"

Question 30

What process occurs in Mitsunobu reaction?

Answer 30

R-OH to R-nuc in one step

Question 31

What kind of nucleophile do you need for Mitsunobu reaction to occur? Give an example.

Answer 31

acidic nucleophile e.g-sulfonamide, carboxylic acid.

Question 32

What happens to the stereochemistry in Mitsunobu?

Answer 32

Inversion of Sn2 stereocentre

Question 33

What is a way to make primary amines?

Answer 33

Use R-N3 and reduce on Pd/C to give primary amine

Question 34

What is the reagent for Gabriel synthesis?

Answer 34

potassium phthalimide

Question 35

What process happens in Gabriel synthesis?

Answer 35

primary amine from alkyl halide