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CHEM 110 > Carboxylic Acid Derivatives > Flashcards

Carboxylic Acid Derivatives Flashcards

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1
Q

How do you name carboxylic acids?

A

Alkanoic acid

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2
Q

How do you name carboxylic ester?

A

Alkyl alkanoate

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3
Q

How do you name acyl (acid) chloride?

A

Alkanoyl chloride

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4
Q

How do you name acid anhydride?

A

Alkanoic anhydride

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5
Q

How do you name amide?

A

Alkanamide

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6
Q

How do you make acyl chlorides?

A

Add SOCl2 to RCOOH

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7
Q

RCOOH + SOCl2

A

ROCl + SO2 + HCl

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8
Q

How do you make acid anhydrides?

A

Add P2O5 to RCOOH

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9
Q

CH3COOH + P2O5

A

CH3COOCOCH3 (symmetrical anhydride) + H3PO4

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10
Q

How do you make ester?

A

Add alcohol and carboxylic acid with acid catalyst

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11
Q

RCOOH + ROH

A

RCOOR + H2O

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12
Q

How do you make amides?

A

RCOOH + RNH2

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13
Q

RCOOH + RNH2?

A

RCONHR + H2O

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14
Q

What is the mechanism for nucleophilic addition?

A

Start off with ketone

Add nucleophile -> electron donated to delta positive C of C=O

Electrons from double bond donated to O -> O gains a negative charge

Add acid -> H+ ion joins to O-

Addition reaction to form alcohol

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15
Q

What is the mechanism for nucleophilic acyl subsitution?

A

Same first step (nucleophile) donates electron to delta positive carbon and electron from double bond donated to oxygen for negative charge

Intermediate forms where the electrons from the oxygen donated back to C-O bond and electron from C-Leaving group donated to leaving group

Forms carboxylic derivative

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16
Q

Which is the slow step for nucleophilic acyl substitution?

A

The initial step in which the carboxylic acid forms the intermediate with negatively charged oxygen

17
Q

What is the order of reactivity for carboxylic acid derivatives?

A

Fastest

Acyl chlorides

Acid anhydrides

Esters

Amides

Slowest

18
Q

How does leaving group strength affect reactivity of carboxylic acid derivatives?

A

It does not

19
Q

What affects the reactivity of carboxylic acid derivatives?

A

The size of the partial positive charge on carbon -> therefore electronegativity of substituent group

This is because the rate determining step of nucleophilic acyl substitution involves the nucleophile and the carboxylic acid derivative

20
Q

How does the electronegativity of the substituent group of carboxylic acid derivatives affect reactivity?

A

If the substituent group is electron donating, the carbon becomes less partially positive meaning it is less reactive

If the substituent group is electron withdrawing, the carbon becomes more partially positive meaning it is more reactive

21
Q

What reactions can acyl chlorides undergo?

A

Acyl chlorides are very reactive due to the electron withdrawing chloride group

Therefore it can form all carboxylic acid derivatives:

  • carboxylic acid
  • acid anhydride
  • amide
  • ester
22
Q

How do you form amide from acyl chlorides?

A

By adding amine

23
Q

How do you form ester from acyl chlorides?

A

By adding alcohol

24
Q

How do you form anhydride from acyl chlorides?

A

By adding carboxylic acid

25
Q

How do you form carboxylic acid from acyl chlorides?

A

By adding water

26
Q

What is the byproduct formed from nucleophilic acyl substitution of acyl chlorides?

A

HCl

27
Q

How do you make an unsymmetrical anhydride?

A

By adding an acyl chloride of different length to a carboxylic acid

28
Q

What carboxylic acid derivatives can anhydrides form?

A

Esters
Amides
Carboxylic acids

NOT acyl halides as they are more reactive

29
Q

What is the byproduct formed from nucleophilic acyl substitution of anhydrides

A

Carboxylic acid

30
Q

What carboxylic acid derivatives can esters form?

A

Amides
Carboxylic acids

NOT acyl halides and anhydrides as they are more reactive

31
Q

How do you hydrolyse esters?

A

Add water with base or acid (either)

Not as reactive as acyl chlorides and anhydrides therefore requires acid or base

32
Q

What carboxylic acid derivatives can amides form?

A

Only carboxylic acids

33
Q

How do you form carboxylic acid from amides?

A

Add 70% (concentrated) sulfuric acid with heat to amide to form protonated amine and carboxylic acid

Adding base to protonated amine will form amine and water

34
Q

What happens when you do nucleophilic acyl substitution using a strong nucleophile in excess?

A

nucleophilic acyl substitution occurs first then

nucleophile added to partial positive carbon form nucleophilic addition in which a nucleophile is added

then acid is added to form the alcohol group

35
Q

What happens when you add LiAlH4 to acyl chloride?

A

Forms an aldehyde RCOH

36
Q

What happens when you add LiAlH4 and acid to an aldehyde?

A

Nucleophilic addition occurs to form ROH

37
Q

How do you make a tertiary alcohol from an acyl chloride?

A

Add grignard reagent to form a ketone (nucleophilic acyl substitution)

Add grignard reagent with acid (nucleophilic addition) to form tertiary alcohol

CHEM 110 (16 decks)

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