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Organic Chemistry II > Ch.20 > Flashcards

Ch.20 Flashcards

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1
Q

_____ acids have an alkyl group bonded to -COOH

A

aliphatic

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2
Q

fatty acids are long-chain ______ ______

A

aliphatic acids

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3
Q

The sp3 oxygen has a C—O—H angle of ______

A

106°

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4
Q

Carboxylic acids boil at considerably _______ temperatures than do alcohols, ketones, or aldehydes of similar molecular weights

A

higher

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5
Q

The high boiling points of carboxylic acids result from what?

A

formation of a stable, hydrogen-bonded dimer

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6
Q

Aliphatic acids with more than ____ carbons are solids at room temperature.

A

eight

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7
Q

How do double bonds effect the melting point?

A

Double bonds (especially cis) lower the melting point

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8
Q

Water solubility _____ with the length of the carbon chain

A

decreases

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9
Q

Acids with more than ____ carbon atoms are nearly insoluble in water

A

10

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10
Q

Carboxylic acids are very soluble in ______

A

alcohols

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11
Q

They are also soluble in relatively _____ solvents like chloroform because the hydrogen bonds of the dimer are not disrupted by the nonpolar solvent

A

nonpolar

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12
Q

acetate ion is _____ stable than an alkoxide ion

A

more

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13
Q

Electron-withdrawing groups _____ the acid strength, and electron-donating groups _______ the acid strength

A

enhance ; decrease

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14
Q

Effects are strongest for substituents in the ____ and ___ positions

A

ortho and para

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15
Q

The hydroxide ion completely deprotonates the acid to form the _______ ______

A

carboxylate salt

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16
Q

how do you name carboxylic acids salts?

A
  1. name the cation
  2. name the anion by replacing the -ic acid with -ate
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17
Q

The basic hydrolysis of ____ and ____ produces soap (this reaction is known as saponification).

A

fats and oils

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18
Q

carboxylic acid protons absorb between what?

A

10 and 13

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19
Q

The protons on the α carbon atom absorb between ____ and ____

A

2.0 and 2.5

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20
Q

The most common fragmentation is the loss of an alkene through the ______ ______

A

McLafferty rearrangement

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21
Q

Another common fragmentation is cleavage of the ____-_____ bond to form an alkyl radical and a resonance-stabilized cation

A

beta-gamma

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22
Q

What can you oxidized primary alcohols and aldehydes with?

A

chromic acid (H2CrO) + H2SO4

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23
Q

Cleavage of an alkene with hot KMnO4 produces what if there is a vinylic hydrogen present?

A

carboxylic acid

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24
Q

How are alkyl benzenes oxidized to benzoic acid?

A

hot KMnO4 or hot H2CrO4

25
Q

How can a primary alcohol (R-CH2-OH) form a carboxylic acid (R-CO-OH)?

A

excess NaOCl, TEMPO

26
Q

What reagents are used to cleave the C=C bond of an alkene (to an acid and ketone)?

A

warm, conc. KMnO4

27
Q

What reagents are used to make alkynes into carboxylic acids?

A

conc. KMnO4 OR
1) O3
2) H20

28
Q

What reagents are used to oxidize side chains of alkylbenzenes (CH3-CH-CH3) –> (COOH)?

A

Na2Cr2O7, H2SO4
heat

29
Q

Grignard reagents react with _____ to produce, after protonation, a carboxylic acid.

A

CO2

30
Q

The carboxylation of grignard reagents increases the number of carbonds in the molecule by ____

A

1

31
Q

What is the Kolbe-Schmidt reaction?

A
  • phenol to 2-hydroxybenzoic acid
  • high pressure (100 atm)
  • high temperature (125C)
32
Q

Basic or acidic hydrolysis of a nitrile (-CN) produces what?

A

carboxylic acid

33
Q

The basic or acidic hydrolysis of nitriles adds how many extra carbons to the molecule?

A

1

34
Q

When an -OH is bonded to an aryl carbon, what is the class of the compound?

A

carboxylic acid

35
Q

When an -Cl is bonded to an aryl carbon, what is the class of the compound?

A

acid chloride

36
Q

When an -OR’ is bonded to an aryl carbon, what is the class of the compound?

A

ester

37
Q

When an -NH2 is bonded to an aryl carbon, what is the class of the compound?

A

amide

38
Q

What is the name of this acid derivative?
R-CO-OH

A

carboxylic acid

39
Q

What is the name of this acid derivative?
R-CO-X

A

acyl halide

40
Q

What is the name of this acid derivative?
R-CO-O-CO-R

A

anhydride

41
Q

What is the name of this acid derivative?
R-CO-O-R’

A

ester

42
Q

What is the name of this acid derivative?
R-CO-NH2

A

amide

43
Q

Carboxylic acids react by ______ _______ _______, where one nucleophile replaces another on the acyl (C=O) carbon atom.

A

nucleophilic acyl substitution

44
Q

What is the order of reactiveness (more reactive to less reactive) of the following acid derivatives: amide, ester, acid chloride, carboxylic acid?

A

acid chloride, ester, amide, carboxylic acid

45
Q

What are the best reagents for converting carboxylic acids to acid chlorides?

A

SOCl2 and COCl2

46
Q

Reduction of a carboxylic acid with an alcohol under acidic conditions produces what?

A

ester

47
Q

What is the formula of diazomethane?

A

CH2N2

48
Q

How are carboxylic acids converted to their methyl esters?

A

adding CH2N2

49
Q

What is the structure of methyl ester?

A

R-CO-O-CH3

50
Q

What are the properties of diazomethane?

A

toxic, explosive, yellow gas

51
Q

Which is more efficient, Fischer esterification or esterification of an acyl chloride?

A

esterification of an acyl chloride

52
Q

The initial reaction of a carboxylic acid with an amine gives an ________ __________ ________.

A

ammonium carboxylate salt

53
Q

What reacts with acid chlorides to give amides?

A

ammonia and amines

54
Q

What reduces carboxylic acids to primary alcohols?

A

LiAlH4

55
Q

BH3 * THF will not reduce a _____

A

ketone

56
Q

What does BH3 * THF reduce carboxylic acids to?

A

primary alcohols

57
Q

Lithium aluminum tri(tert-butoxy)hydride is a _______ reducing agent than lithium aluminum hydride.

A

weaker

58
Q

Why does lithium aluminum tri(tert-butoxy)hydride reduce acid chlorides?

A

they are strongly activated toward nucleophilic addition of a hydride ion

Organic Chemistry II (8 decks)

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