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CHEM2103 > Week 1 and 2 Reactions > Flashcards

Week 1 and 2 Reactions Flashcards

1
Q

R-X + Mg, Et2O —>

A

R-Mg-X

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2
Q

R-X + 2 Li
What is the product?
What is this reaction called?

A

LiX + R-Li
Oxidative Insertion

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3
Q

R-X + Mg.
What is the product?
What is this reaction called?

A

R-Mg-X
Oxidative Insertion

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4
Q

Grignard plus formaldehyde

A

primary alcohol

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5
Q

Grignard plus aldehyde

A

secondary alcohol

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6
Q

grignard plus ketone

A

tertiary alcohol

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7
Q

what determines hydrocarbon acidity?

A

The more stable the conjugate base, the stronger the acid. Lower pka means stronger acid

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8
Q

what is the relationship between pka of HX and leaving group ability?

A

lower the pka of HX, better the leaving ability of X-

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9
Q

what is the relationship between the pka of AH and nucleophilicity?

A

Higher the pka, the better the nucleophilicity of A-

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10
Q

What are the 3 ways to make an ester from an alcohol

A
  1. Acyl chlorides
  2. Acid anhydrides
  3. carboxylic acids
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11
Q

How to make:
acid chloride from carboxylic acid

A

add SOCl2 or PCl5

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12
Q

How to make:
carboxylic acid from acid chloride

A

add water

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13
Q

how to make:
amine from acid chloride

A

add nh3

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14
Q

how to make:
ester from acid chloride

A

add alcohol

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15
Q

how to make:
carboxylic acid from ester

A

add water and acid/base

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16
Q

how to make:
ester from carboxylic acid

A

add acid

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17
Q

How to make:
carboxylic acid from amine

A

add water and strong acid/base

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18
Q

how to turn ester into tertiary alcohol

A

add 2 x Grignard and acid

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19
Q

ester + lialh4

A

primary alcohol

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20
Q

Name 2 keys ways to make ketones from esters

A
  1. Start with more reactive carboxylic acid derivative (or transmetallation with copper)
  2. make product/intermediate more stable
21
Q

How can we make intermediate more stable to turn ester into ketone

A
  1. use lithium carboxylates
  2. weinreb amides
  3. use DMF to make aldehyde
  4. use nitrile
22
Q

what is the relationship between base and nucleophilicity

A

bases make alcohols more nucleophilic

23
Q

what is the relationship between acids and electrophilicty

A

acids make aldehydes more electrophilic

24
Q

what is the relationship between aldehydes, hemiacetals and acetals

A

aldehyde+ alcohol + acid/base -> hemiacetal -> (add more alcohol/acid/base) —> acetal

25
Q

why are imines unstable in water

A

c=o stronger than C=N

26
Q

how are imines made?

A

aldehyde/ketone + primary amine

27
Q

how are enamines made?

A

aldehyde/ketone + secondary amine

28
Q

what are 2 examples of stable imines

A

oxime
hydrazone

29
Q

what is the best reducing agent for reductive animation

A

NaCNBH3

30
Q

Benzene-bromide + butyl-lithium. What is the product? What is this reaction?

A

Benzene-lithium + butyl-bromide. Metal halogen exchange

31
Q

What reagents are common in a transmetallation reaction

A

Use mg and eto2 to make grignard. Then add ZnBr2 in THF

32
Q

Acid chloride plus alcohol

A

Ester plus acid

33
Q

Anhydride plus alcohol

A

Ester plus carboxylic acid

34
Q

Carboxylic acid plus alcohol

A

Ester and water

35
Q

What are the steps in using lithium carboxylates into ketones?

A
  1. Carboxylic acid plus RLi to swap H for Li
  2. Add more RLi to add Li to double bond O
  3. Add acid
  4. Final product has R where OH used to be
36
Q

Weinreb amide plus acyl chloride

A

Put r group from amide in spot of Cl. Reagents are the amide and acid

37
Q

How to use nitrile to make ketone

A
  1. Nitrile = has a CN group
  2. Other reagent will be grignard with MgBr and R group
  3. C from the nitrile gets double bond O and R group attached to make ketone
38
Q

Benzene with aldehyde attachment plus R with NH2 attachment

A

Benzene with double bond N attachment with R attachment

39
Q
  1. Ketone plus Nh2 with R group
  2. Add NaBh4 and water
A
  1. Subtract a water molecule. Double bond o replaced by double bond N with R group
  2. Break double bond N and add a H
40
Q

What is a strecker synthesis

A
  1. React aldehyde with NaCN and Nh4Cl
  2. Product: swap double bond o for Nh2 and swap h for CN
  3. React further with acid and water
  4. Product: turn Nh2 into nh3 and swap CN for carboxylic acid
41
Q

Acid chloride plus carboxylic acid

A

Anhydride

42
Q

Carboxylic acid plus LiAlH4

A

Alcohol

43
Q

Amide plus LiAlh4

A

Amine

44
Q

Ketone plus NaCN, H20 and Nh4Cl

A

Swap double bond O for Nh2. Add CN attachment to the double bond carbon

45
Q

OMe group plus HCl and water

A

Turn OMe into OH group with squiggle bond

46
Q

2 OH groups next to each other on chair structure plus formaldhyde and TsOH (-H20)

A

Loose the H’s, cross over the bonds from the O and add an extra CH3 group to each O

47
Q

NH with 2 R groups plus aldehyde and NaCNBH3

A

Take away H from aldehyde and NH and make the remaining aldehyde group and attachment on the N

48
Q

Organic with Nh2 and CN group coming from same carbon plus water and acid

A

Turn Nh2 into Nh3. Turn CN into carboxylic acid

49
Q

Aldehyde plus OH-NH2

A

Turn double bond O into double bond N with OH group coming off N using squiggle bond

CHEM2103 (4 decks)

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