Klein - 21

Front 1

Acetic acid

Back 1

Front 2

Butanoic acid

Back 2

Front 3

Lactic Acid

Back 3

Front 4

Formic acid

Back 4

Front 5

Butyric acid

Back 5

Front 6

Name following compound?

Back 6

Front 7

Oxalic acid

Back 7

[memorize: ~oskol =>just two aceticacid group attached to each other]

Front 8

Malonic acid

Back 8

[memorize: ~mal => 2 be 1 malidan]

Front 9

Succinic acid

Back 9

[Memorize: suski ke docharkhe savar mishe]

Front 10

Write down Henderson-Hasselbalch equation to calculate pH of buffered solutions?

Back 10

Front 11

If an acide dissolved in a buffered solution, when the pH of the buffere solution is equal to pKa of the acide, what is the ratio of the acid and its conjugate base?why?

Back 11

An acid and its conjugate base will be present in approximately equal amounts (due to Henderson-Hasselbalch equation for calculation of pH of a buffer)

Front 12

carboxylic acids will exist primarily as …… (caroxylic acid / carboxylate salts) at physiological pH. Why?

Back 12

carboxylate salts (because according to Henderson-Hasselbalch equation concentration of conjugate would be 1000 times more than acid. Notice Pka of most of carboxylic acids is between 4 and 5):

Front 13

How to convert alkyl halides to carboxylic acids with one more carbon?

Back 13

1.SN2 reaction with CN- /2.Acidic hydrolysis of CN group

Front 14

How we can make carboxylic acids from grignard reagents?

Back 14

Reacting with CO2

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Back 15

Borane can selectively reduce carboxylic acids to alcohols

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Back 16

borane reduces selectively a carboxylic acid moiety in the presence of another carbonyl group

Front 17

Name four major groups of carboxylic acid derivatives?

Back 17

Acid halides, Acid anhydrides, Esters, Amides

Front 18

What is the result of acidic hydrolysis of carboxylic acid derivatives? a.acide chlorides b. acid anhydrides c.esters d.amides

Back 18

All will be converted to their corresponding carboxylic acid

Front 19

Acid halide?

Back 19

Front 20

Acid anhydride

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Front 21

Ester

Back 21

Front 22

Amide

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Front 23

Nitrile

Back 23

Front 24

Are nitriles considered as carboxylic acid derivatives? Why?

Back 24

Yes. Because like carboxylic acids the central carbon has three bonds to more electronegative elements therefore has the same oxidation state as carboxylic acid

Front 25

Succinic anhydride

Back 25

Front 26

Acetamide

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Amide made from acetic acid

Front 27

Benzamide

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Front 28

N-Methyl acetamide

Back 28

Front 29

Benzonitrile

Back 29

A nitrile derivated from benzoicacid

Front 30

Rank acid halides, acid anhydrides, esters and amides according to reactivity toward nucelophiles?

Back 30

Acid halides > ancid anhydride > Esters > Amides (due to ability to contribute to stabilize positive charge by resonance)

Front 31

Discuss the possibiblity of the conversion of four major carcboxylic acid derivates to each other by a simple acyl substitution?

Back 31

the more reactive carboxylic acid derivatives can be converted to the less reactive derivative by a simple acyl subsitution . (Acid chlorides can be converted to acid anhydrides, esters and amides / acid anhydrides can be convereted to esters and amides/ Esters can be converted to amindes )

Front 32

What is the hybridization of nitrogen in amides? Why? What geometry they adapt?

Back 32

Sp2 (not sp3! As expected because in resonance structure The p orbital on the carbon atom effectively overlaps with
a p orbital on the nitrogen atom) =>trigonal planar

Front 33

Define nucleophilic acyl substitution?

Back 33

Where z is a good leaving group (not H and R)

Front 34

Explain when nucleophilic attack on C=O leads to and addition and when to a substitution?

Back 34

When a nucleophile attacks a carbonyl group to form a tetrahedral intermediate, the carbonyl group
will always be re-formed, if possible, but H– and C– are never expelled as leaving groups

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Back 35

Formation of acid chlorides

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Back 36

Name: Acylation of OH group or Alcoholysis of Acid chlorides or (acyl substitution)

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Back 37

Name: Acylation of OH group (acyl substitution) is sensitive to steric hindrance so primary is preferred over secondary

Front 38

What is the result of Aminolysis of Acid Chlorides?

Back 38

formation of Amides

Front 39

LiAlH4 is a very strong hydride reducing reagent. Propose a hydride reducing reagent which is moderate (for exmaple reduces acid chlorides to aldehyes not all the way down to alcohol?

Back 39

tri(t-butoxy) aluminum hydride (bulky and just one mole of hydride exists. Unlike LiAlH4 which has four hydrides)

Front 40

What is DIBAH? What is good for?

Back 40

DIBAH = diisobutylaluminiumhydride / it's a moderate reducing reagentso it just able do acyl substitution on carboxylic acid derivtives to give aldehydes (unlike LiAlH4 which goes all the way down to an alcohol)

Front 41

Back 41

Acyl substation by LiAl(OR)3H (which is a mild hydride reducing reagent so it won't recduce the C=O all the way down to an alcohol. It stops at aldehyde)

Front 42

What's Gilman reagent? What is used for?

Back 42

A lithium dialkyl cuprate. It provide carbon nuclephiles with mild reactivity which can perform substitution on C=O but not addtion.

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Back 43

two Nuclephilic attack of the carbon nucleophile of Grignard reagent (1.acyl substitution and then addition 2.protonation)

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Back 44

Reaction of C=O with Gilman reagent. (carbon nucleophile of Gilman reagent is not as strong as carbon nucleophile of Grignard reagent so it is just able to do acyl subsitution but not addition)

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Back 45

Acyl substitution. (the more reactive carboxylic acid derivatives can be converted to the less reactive derivative by a simple acyl subsitution . e.g. Esters can be made from acid anydrides)

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Back 46

1. Deprotonatin 2.Simple SN2 reaction

Front 47

Define Fischer esterification?

Back 47

Carboxylic acids are converted into esters when treated with an alcohol in the presence of an acid catalyst. This process is called the Fischer esterification

Front 48

Define saponification?

Back 48

Esters can be converted into carboxylic acids by treatment with sodium hydroxide followed by an acid.

Front 49

In the following Fischer esterification explain wehere the 18O would be in the product?

Back 49

Since RO attackes, 18O would be in the ester and carboxylic acid OH will turn to water

Front 50

Explain place of 18O in the products in the following saponification reaction?

Back 50

Since OH attacks to make tetrahderal and then RO kicks out, 18O with be in ROH

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Back 51

DIBAH = moderate hydride reducing reagent (1.just one acyl substitution / 2.protonation)

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Back 52

Acyl substittion (Amides can be prepared from any of the other 3 carboxylic acid derivatives because it is the least reactive one)

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Basic hydrolysis of amides (which like acidic hydrolysis yields carboxylic acids)

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Preparation of nitriles from amids

Front 55

What would be the result of acidic (H3O+) or basic (1.NaOH, H2O 2.H3O+) hydrolysis of nitriles?

Back 55

Carboxylic acids (e.g. the following basic reaction)

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Back 56

1. Creation of imine (by a nucleophililic attack) 2.acidic hydrolysis of imines

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1. Creation of imine (by a nucleophililic attack) 2.acidic hydrolysis of imines

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1.two successive Hydride attack 2.protonation (of nitrogen)

Front 59

Explain C-C bond forming reactions of carboxylic acid derivatives?

Back 59

a. Making C-C connection b. makind C-C connection with an extra carbon

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Back 60

Amides in the presence of LAlH4 are reduced to CH2 (against expectation of hydride attack on C=O)