Week 1 and 2 Reactions

Question 1

R-X + Mg, Et2O —>

Answer 1

R-Mg-X

Question 2

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

Answer 2

LiX + R-Li
Oxidative Insertion

Question 3

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

Answer 3

R-Mg-X
Oxidative Insertion

Question 4

Grignard plus formaldehyde

Answer 4

primary alcohol

Question 5

Grignard plus aldehyde

Answer 5

secondary alcohol

Question 6

grignard plus ketone

Answer 6

tertiary alcohol

Question 7

what determines hydrocarbon acidity?

Answer 7

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

Question 8

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

Answer 8

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

Question 9

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

Answer 9

Higher the pka, the better the nucleophilicity of A-

Question 10

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

Answer 10

1. Acyl chlorides
2. Acid anhydrides
3. carboxylic acids

Question 11

How to make:
acid chloride from carboxylic acid

Answer 11

add SOCl2 or PCl5

Question 12

How to make:
carboxylic acid from acid chloride

Answer 12

add water

Question 13

how to make:
amine from acid chloride

Answer 13

add nh3

Question 14

how to make:
ester from acid chloride

Answer 14

add alcohol

Question 15

how to make:
carboxylic acid from ester

Answer 15

add water and acid/base

Question 16

how to make:
ester from carboxylic acid

Answer 16

add acid

Question 17

How to make:
carboxylic acid from amine

Answer 17

add water and strong acid/base

Question 18

how to turn ester into tertiary alcohol

Answer 18

add 2 x Grignard and acid

Question 19

ester + lialh4

Answer 19

primary alcohol

Question 20

Name 2 keys ways to make ketones from esters

Answer 20

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

Question 21

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

Answer 21

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

Question 22

what is the relationship between base and nucleophilicity

Answer 22

bases make alcohols more nucleophilic

Question 23

what is the relationship between acids and electrophilicty

Answer 23

acids make aldehydes more electrophilic

Question 24

what is the relationship between aldehydes, hemiacetals and acetals

Answer 24

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

Question 25

why are imines unstable in water

Answer 25

c=o stronger than C=N

Question 26

how are imines made?

Answer 26

aldehyde/ketone + primary amine

Question 27

how are enamines made?

Answer 27

aldehyde/ketone + secondary amine

Question 28

what are 2 examples of stable imines

Answer 28

oxime hydrazone

Question 29

what is the best reducing agent for reductive animation

Answer 29

NaCNBH3

Question 30

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

Answer 30

Benzene-lithium + butyl-bromide. Metal halogen exchange

Question 31

What reagents are common in a transmetallation reaction

Answer 31

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

Question 32

Acid chloride plus alcohol

Answer 32

Ester plus acid

Question 33

Anhydride plus alcohol

Answer 33

Ester plus carboxylic acid

Question 34

Carboxylic acid plus alcohol

Answer 34

Ester and water

Question 35

What are the steps in using lithium carboxylates into ketones?

Answer 35

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

Question 36

Weinreb amide plus acyl chloride

Answer 36

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

Question 37

How to use nitrile to make ketone

Answer 37

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

Question 38

Benzene with aldehyde attachment plus R with NH2 attachment

Answer 38

Benzene with double bond N attachment with R attachment

Question 39

1. Ketone plus Nh2 with R group 2. Add NaBh4 and water

Answer 39

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

Question 40

What is a strecker synthesis

Answer 40

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

Question 41

Acid chloride plus carboxylic acid

Answer 41

Anhydride

Question 42

Carboxylic acid plus LiAlH4

Answer 42

Alcohol

Question 43

Amide plus LiAlh4

Answer 43

Amine

Question 44

Ketone plus NaCN, H20 and Nh4Cl

Answer 44

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

Question 45

OMe group plus HCl and water

Answer 45

Turn OMe into OH group with squiggle bond

Question 46

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

Answer 46

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

Question 47

NH with 2 R groups plus aldehyde and NaCNBH3

Answer 47

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

Question 48

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

Answer 48

Turn Nh2 into Nh3. Turn CN into carboxylic acid

Question 49

Aldehyde plus OH-NH2

Answer 49

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