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Organic Chemistry > Carboxylic Acids & their derivatives cont > Flashcards

Carboxylic Acids & their derivatives cont Flashcards

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1
Q

When a nucleophile attacks a carbonyl group to form a _______________ the carbonyl group will always be re-formed if possible but H-(hydride) & C- (carbanion) are generally not used as leaving groups

A

Tetrahedral intermediate

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2
Q

What are the two core steps in a nucleophilic acyl substitution?

A
  1. Nucleophilic attack
  2. Loss of LG
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3
Q

In _______ conditions avoid formation of a strong base & in _______ condition such as hydroxide or methoxide avoid formation of a strong acid

A

Acidic, Basic

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4
Q

What is the mechanism pattern for reactions dealing with acid halides?

A
  1. Nucleophilic attack
  2. Loss of LG
  3. Proton transfer
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5
Q

Acid chlorides can be formed by treating carboxylic acids with _________

A

Thionyl chloride (SOCl2)

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6
Q

When treated with water acid chloride are hydrolyzed to form ___________

A

Carboxylic acid

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7
Q

When treated with alcohol acid chlorides are converted into ___________

A

Esters

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8
Q

When converting acid halides into alcohols can looks from the alcohol point of view and see that the alcohol undergoes ___________

A

Acylation

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9
Q

When two alcohols are present the acyl group attack the ___________ position

A

less sterically hindered

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10
Q

Aminolysis of acid chlorides

A

When treated with ammonia (NH3) acid chlorides are converted into amides

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11
Q

___________ of acid chlorides has the same mechanism as hydrolysis of an acid chloride

A

Aminolysis

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12
Q

When treated with lithium aluminum hydride (LAH) acid chlorides are reduced to form ___________

A

Alcohols

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13
Q

When acid chlorides are treated with lithium tri(t-butoxy) aluminum hydride (LiAl(OR)3H) its converted into an ___________

A

Aldehyde

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14
Q

When treated with Grignard reagent acid chlorides are converted in to ___________

A

Alcohols

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15
Q

When acid chlorides are treated with lithium dialkyl cuprate (R2CuLi)(Gilman reagent) its converted into a ________

A

Ketone

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16
Q

Acetic acids can be converted into __________ with excess heat

A

Acid anhydrides

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17
Q

_________________ can also be formed by treating an acid chloride with a carboxylate ion

A

Anhydride

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18
Q

Reaction for anhydrides are the same as reaction for ______________ (Only difference is the LG for acid chloride is Cl & for anhydride its a carboxylate ion)

A

Acid chloride

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19
Q

____________ are better starting material than acid anhydrides because you only lose a halide & not half of the starting material

A

Acid halides

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20
Q

When treated with a strong base followed by alkyl halide, a carboxylic acid is converted into ___________

A

Esters

21
Q

Fischer esterification

A

When carboxylic acids are converted into ester when treated with an alcohol in the presence of an acid catalyst

22
Q

Esters can also be prepared by treating an acid chloride with an ___________

A

Alcohol (ROH/py)

23
Q

Saponification

A

Esters being treated with sodium hydroxide followed by an acid to be converted into carboxylic acids (NaOH/H3O+)

24
Q

Esters can also be hydrolyzed under acidic conditions (H3O+) to produce _________

A

Alcohols

25
Q

Esters can react with amines (NH3) to produce __________

A

Amides

26
Q

When esters are treated with LAH they are reduced to form __________

A

Alcohols

27
Q

Esters can be reduced with DIBAH to make ___________

A

Aldehydes

28
Q

When esters are treated with Grignard reagents they are reduced to make ________ with alkyl groups

A

Alcohols

29
Q

__________ can be produced from any of the carboxylic acid derivatives

A

Amides

30
Q

Acid chlorides are mostly used to make _________

A

Amides

31
Q

When amides are treated with aqueous acid (H3O+) they are reduced to make ____________

A

Carboxylic acids

32
Q

Amides are hydrolyzed when treated in basic aqueous solution (like NaOH/H3O+) to make ___________

A

Carboxylic acid

33
Q

When treated with xs LAH amides are converted into __________

A

Amines

34
Q

________ can be prepared by treating an alkyl halide with a cyanide ion (NaCN) (SN2 reaction so no tertiary alkyl halide)

A

Nitriles

35
Q

_________ can also be made via dehydration of an amide with SOCl2

A

Nitriles

36
Q

When treated with aqueous acidic (H3O+) nitriles are hydrolyzed to make ______ which are further hydrolyzed to make ________

A

Amides, Carboxylic acid

37
Q

Nitriles can also be hydrolyzed in aqueous basic condition (NaOH, H2O) to produce ___________

A

Carboxylic acids

38
Q

When nitrile is treated with a Grignard reagent a _______ is formed

A

Ketone

39
Q

Nitriles are converted in to _______ when treated with LAH

A

Amines

40
Q

What are the two types of C-C bond-forming reactions?

A
  1. C-C bonds formation where the functional group stayed in the same place
  2. C-C bond forming reaction where the functional group position changed
41
Q

What is wavenumber for acid chloride in IR spectrum?

A

1800

42
Q

What is wavenumber for anhydride in IR spectrum?

A

1760 & 1820

43
Q

What is wavenumber for carboxylic acid in IR spectrum?

A

1760

44
Q

What is wavenumber for ester in IR spectrum?

A

1740

45
Q

What is wavenumber for ketone in IR spectrum?

A

1720

46
Q

What is wavenumber for amide in IR spectrum?

A

1660

47
Q

The carbonyl group of a carboxylic acid derivative signal is between __________ in 13C spectrum

A

160-185ppm

48
Q

The carbon atom in a nitrile produces a signal around _________ in 13C spectrum

A

115-130 ppm

49
Q

The proton of a carboxylic acid usually produces a signal around _______ in HNMR

A

12ppm

Organic Chemistry (47 decks)

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