Quiz 5

Question 1

What is the difference between enamine and imine formation?

Answer 1

Enamine formation is different in the last proton transfer step that creates the C=C bond of an enamine

Question 2

LiAlH and NaBH4 are —- —

Answer 2

reducing agents

Question 3

True or false?

LAH will not reduce carboxylic acids or esters

Answer 3

false, it is strong enough to react with them but NaBH4 is not

Question 4

The grignard reagent is a — —-

Answer 4

reducing agent

Question 5

What is necessary to react a carboxylic acid with a grignard reagent?

Answer 5

a blocking group on the acidic proton

Question 6

Cyanohydrin

Answer 6

CN + OH attatched to the same carbon

Question 7

Aldehydes + ketones reacted with HCN will yield a —-

Answer 7

cyanohydrin

Question 8

Wittig Reaction

Answer 8

reduces a ketone to an alkene

C=O bond to C=C bond

Question 9

How do you form the wittig reagent/ ylide?

Answer 9

P(Ph)3 + alkly halide
pt
- SN2 like process, akyl halide must be primary or secondary

Question 10

Where does the carbon of the new C=C bond come from in the wittig reaction?

Answer 10

the akyl halide reacting to form the ylide

Question 11

Bayer Village oxidation

Answer 11

peroxyacetic acid + ketone or aldehyde to form a ester

Question 12

What is the preference for where the oxygen is moved to for the bayer village reaction?

Answer 12

H>3>2>ph>1> methyl

left: easiest to move right: hardest to move

Question 13

What is the suffix for compounds with one carb acid?

Answer 13

-oic acid

Question 14

What is the suffix for compounds with two carb acids?

Answer 14

-dioic acid

Question 15

What is the suffix for carboyxlate ions?

Answer 15

-oate

Question 16

Why do carb acids have high bps?

Answer 16

because they can form two hydrogen bonds between each other

Question 17

In water does the reaction favor a carb acid or H3O+?

Answer 17

carb acid bc it is weaker than H3O+ and reactions favor moving away from the strongest acid

Question 18

Do halogens stabilize or de stabilize a carb acid?

Answer 18

stabilize, bc they are ewg

Question 19

alkyne + O3 and H3O+ =

Answer 19

2 carboxlyic acids

Question 20

primary alcohol + KMnO4/Chromic acid =

Answer 20

carboxylic acid

Question 21

Reagents and products of oxidation of an alkyl benzene

Answer 21

reagents: chromic acid +H2SO4
products: benzoic acid

Question 22

R-CN + H3O+ + heat =

Answer 22

carboxylic acid

new way to make carb acids

Question 23

CO2 + grignard reagent =

Answer 23

carboxlyic acid

a new way to make carb acids

Question 24

What reagents can be used to reduce a carb acid to an alcohol?

Answer 24

LAH or BH3 . THF and grignard reagent

Question 25

Mechanism of the reduction of carb acid to an alcohol

Answer 25

1. pt to create carboxylate 2. Elimination to form aldehyde intermediate 3. nuc attack by H- 4. pt to create neutral product

Question 26

Derivatives of carb acids

Answer 26

molecules that look like carb acids but the OH group has been replaced with something else

Question 27

What are the 5 carb acid derivatives we have been introduced to?

Answer 27

1. acid halide 2. acid anhydride 3. ester 4. amide 5. nitrile

Question 28

suffix for acid halide

Answer 28

-yl halide

Question 29

suffix for acid anhydride

Answer 29

-anhydride

Question 30

suffix for amide

Answer 30

-amide

Question 31

Suffix for nitriles

Answer 31

-onitrile

Question 32

Nucleophilic acyl substitution

Answer 32

nucleophilic attack on a carb acid derivative to replace good LG

Question 33

What is the intermediate of Nucleophilic Acyl substitution?

Answer 33

tetrahedral intermediate

Question 34

What charges can form in acidic conditions?

Answer 34

positive or overall neutral

Question 35

What charges can form in basic conditions?

Answer 35

negative or over all neutral

Question 36

# True or False? C- and H- make good leaving groups because they are good nucleophiles?

Answer 36

false, they rarely make good leaving groups

Question 37

Where are the three places an extra pt step can occur in nucleophilic acyl substitution?

Answer 37

1. before nuc attack 2. between nuc attack and LLG 3. after LLG

Question 38

Why would a pt step occur before nuc attack in nucleophilic acyl substitution?

Answer 38

If the reagents are acidic

Question 39

Why would a pt step occur between LLG and nuc attack in nucleophilic acyl substitution?

Answer 39

if the LG needs to be protonated in order to leave

Question 40

Why would a pt step have to occur after LLG?

Answer 40

if the nucleophile was neutral and the final product needs to be neutralized

Question 41

How do you prepare an acid chloride

Answer 41

treatment of a carb acid with SOCl2

Question 42

Hydrolysis of acid halides/ anhydrides

Answer 42

acid halide/ anhydride + water = carb acid +HCl

Question 43

alcoholysis of acid halides/anhydrides

Answer 43

ROH and pyridine + acid halide/anhydride = ester

Question 44

# ` Aminolysis of acid halides/ acid anhydrides

Answer 44

2 eq of NH3 + Acid halide/anhydride = amide

Question 45

Why is pyridine not used in aminolysis of acid anhydrides/halides?

Answer 45

Bc NH3 is strong enough to neutralized HCl on its own

Question 46

Reduction of acid halides/ acid anhydrides

Answer 46

acid halide/anhydride + LAH or grignard reagent = alcohol

Question 47

What does LiAl(OR)3H do?

Answer 47

in a reduction of a acid halide/anhyrdie with LAH it will stop it at the aldehyde intermediate

Question 48

What does the Gilman reagent/R2CuLi do?

Answer 48

in the reduction of an acid halide/acid anhydride with a grignard reagent it will stop it at the ketone intermediate