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MLC Lectures > Handout 2 Material > Flashcards

Handout 2 Material Flashcards

1
Q

What is the reactivity series of functional groups

A

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

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2
Q

Why do we use weakest reducing agent for functional group?

A

To avoid side reactions

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3
Q

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

A

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

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4
Q

What is special about the BHTF mechanism?

A

Form borate ester which goes on to react further

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5
Q

What happens when you reduce ester with LiALH4?

A

You get primary alcohol

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6
Q

What are some common oxidising agents?

A

potassium dichromate, potassium permanganate, Jones reagent

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7
Q

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

A

PCC

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8
Q

How do you convert primary alcohol to aldehyde?

A

Swern oxidation

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9
Q

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

A

H2NNH2 and ketone to corresponding alkane

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10
Q

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

A

ketone to ester using MCPBA

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11
Q

What are the products of the Swern oxidation?

A

Me2S and aldehyde

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12
Q

What are the reagents in the Clemmenson reaction?

A

zinc mercury amalgam and HCl

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13
Q

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

A

Carbocation stability

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14
Q

What happens to stereochemistry in Bayer-Villiger reaction?

A

Retention of stereochemistry

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15
Q

How do you convert carboxylic acid to acid chloride?

A

Thionyl chloride or PCl5

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16
Q

What happens when you react a carboxylic acid with base?

A

An Sn2 can occur

17
Q

What is the product of carboxylic acid and diazomethane?

A

ester and nitrogen gas

18
Q

How can you convert an acid chloride to an amide?

A

reaction of amine and acid chloride

19
Q

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

A

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

20
Q

Does DMAP or DCC react faster with a nucleophile?

A

DMAP

21
Q

How do you reduce an amide to nitrile?

A

thionyl chloride

22
Q

How do you convert nitrile to carboxylic acid?

A

acid/H20 and heat

23
Q

What is the product of an amine reduction using LiAlH4?

A

amine

24
Q

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

A

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

25
Q

What are the reagents for reductive amination?

A

NaBH(OAc)3 or NaBH3CN

26
Q

What is the process of reductive amination?

A

tertiary amine from carboxylic acid and amine via amine

27
Q

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

A

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

28
Q

What are some other methods to make alkyl halides?

A

Tosylates then Sn2

Use SoCl2 or PBr3 also Sn2 like reaction

29
Q

What are the reagents for Mitsunubu reaction?

A

“DEAD”

30
Q

What process occurs in Mitsunobu reaction?

A

R-OH to R-nuc in one step

31
Q

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

A

acidic nucleophile e.g-sulfonamide, carboxylic acid.

32
Q

What happens to the stereochemistry in Mitsunobu?

A

Inversion of Sn2 stereocentre

33
Q

What is a way to make primary amines?

A

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

34
Q

What is the reagent for Gabriel synthesis?

A

potassium phthalimide

35
Q

What process happens in Gabriel synthesis?

A

primary amine from alkyl halide

MLC Lectures (2 decks)

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