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2023-2024 > Carboxylic Acids - Chp 20 > Flashcards

Carboxylic Acids - Chp 20 Flashcards

1
Q

Increasing stability of the C.B, increases what? Smaller or lower pKa?

A

The acidity; Smaller pKa

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2
Q

Does resonance always increase stability of C.B?

A

No, not always, it depends on the location of the anion.

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3
Q

Electron-withdrawing groups ________ C.B, making carboxylic acid _______ acidic

A

stabilize; more

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4
Q

Electron donating groups __________ C.B, making carboxylic acid _______ acidic.

A

destabilize; less

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5
Q

Electron-withdrawing groups ________ the acid strength, and electron-donating groups _________ the acid strength.

A

enhance; decrease

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6
Q

What effects are strongest for substituents positions?

A

Ortho and para positions.
(ortho > para with the same substituent)

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7
Q

Oxidation of alcohol and aldehyde with what reagent produces a carboxylic acid.

A

Chromic acid (H2CrO4) or NaOCl

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8
Q

Naming a carboxylic acid involves removing the ā€œeā€ from an alkane/alkene and adding ____.

A

-oic acid

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9
Q

Compounds containing 2 carboxy groups are called what?

A

Diacids
ex. ethanedioic acid

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10
Q

For naming metal salts what suffix do you add?

A

-ate
ex. sodium propanate

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11
Q

The high boiling points of carboxylic acids result from what?

A

The formation of a stable,
hydrogen-bonded dimer.

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12
Q

Do double bonds increase or decrease the melting point? Does cis or trans affect it more?

A

Decrease; especially cis

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13
Q

Acids with more than 10 carbon atoms are nearly __________ (soluble/insoluble)

A

insoluble.

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14
Q

Which is more stable between acetate ion and alkoxide ion? Why?

A

Acetate ion because the delocalization of the negative charge over the two oxygens makes it more stable than an alkoxide ion.

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15
Q

Having the negative charge on C instead of O is less or more stable? Why?

A

Less stable b/c C is less electronegative.

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16
Q

What 3 things can make an acid stronger?

A

Increase number of electronegative substituents, the more electronegative substituent (compared to another atom), the closer the electron withdrawing group to the COOH.

17
Q

Primary alcohol, aldehyde and H2CrO4 produces what?

A

Carboxylic acid

18
Q

Cleavage of an alkene with hot KMnO4 produces a carboxylic
acid with what reagent is present?

A

A vinylic hydrogen present

19
Q

Primary alcohol or aldehyde with what reagent produces a carboxylic acid?

A

Na2Cr2O7, H2SO4

20
Q

Ozonolysis of an alkyne produces what? What reagents are used?

A

A carboxylic acid group; conc. KMnO4 or 1. O3 2. H2O

21
Q

Alkyl benzenes with KMnO4 and heat produces what?

A

Benzoic acid.

22
Q

Alkene with hot KMnO4 and a vinylic hydrogen produces what?

A

A carboxylic acid and a ketone.

23
Q

How to produce a carboxylic acid from an alkyl or aryl halide?

A

With a Grignard reagent, CO2 and H+

24
Q

A nitrile reacting with what reagent produces a carboxylic acid?

A

H+, H2O or OH- (Hydrolysis)

25
Q

Reaction of a carboxylic acid with _______ under acidic conditions produces an ester. (Fisher Esterification)

A

alcohol

26
Q

True or false. Esterification of a carboxylic acid occurs in the presence of acid but not in the presence of base.

A

True, only the presence of acids (not bases like OH-)

27
Q

How are carboxylic acids converted to methyl esters?

A

By adding/reacting with diazomethane(N=N=CH2).

28
Q

LiAlH4 and H3O+ reduces carboxylic acids to ________.

A

primary alcohols

29
Q

Borane (BH3.THF) can reduce a __________ to _________.

A

a carboxylic acid; alcohol

30
Q

What reagent is used to convert COOH to a ketone?

A

2R-Li and H2O
ex. CH3CH2-Li and H2O

31
Q

Are alcohol soluble?

A

Yes, very soluble.

32
Q

As the length of the carbon chain increase, water solubility _______.

A

decreases

33
Q

What reagent is used to convert a carboxylic acid to an acid chloride?

A

SOCl2 or C2O2Cl2

34
Q

Carboxylic acid reacting with SOCl2 produces __________.

A

An acid choride.

2023-2024 (18 decks)

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