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Organic Chemistry II > Ch.20 > Flashcards

Ch.20 Flashcards

(58 cards)

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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?

Study These Flashcards
A

hot KMnO4 or hot H2CrO4

25
How can a primary alcohol (R-CH2-OH) form a carboxylic acid (R-CO-OH)?
excess NaOCl, TEMPO
26
What reagents are used to cleave the C=C bond of an alkene (to an acid and ketone)?
warm, conc. KMnO4
27
What reagents are used to make alkynes into carboxylic acids?
conc. KMnO4 OR 1) O3 2) H20
28
What reagents are used to oxidize side chains of alkylbenzenes (CH3-CH-CH3) --> (COOH)?
Na2Cr2O7, H2SO4 heat
29
Grignard reagents react with _____ to produce, after protonation, a carboxylic acid.
CO2
30
The carboxylation of grignard reagents increases the number of carbonds in the molecule by ____
1
31
What is the Kolbe-Schmidt reaction?
- phenol to 2-hydroxybenzoic acid - high pressure (100 atm) - high temperature (125C)
32
Basic or acidic hydrolysis of a nitrile (-CN) produces what?
carboxylic acid
33
The basic or acidic hydrolysis of nitriles adds how many extra carbons to the molecule?
1
34
When an -OH is bonded to an aryl carbon, what is the class of the compound?
carboxylic acid
35
When an -Cl is bonded to an aryl carbon, what is the class of the compound?
acid chloride
36
When an -OR' is bonded to an aryl carbon, what is the class of the compound?
ester
37
When an -NH2 is bonded to an aryl carbon, what is the class of the compound?
amide
38
What is the name of this acid derivative? R-CO-OH
carboxylic acid
39
What is the name of this acid derivative? R-CO-X
acyl halide
40
What is the name of this acid derivative? R-CO-O-CO-R
anhydride
41
What is the name of this acid derivative? R-CO-O-R'
ester
42
What is the name of this acid derivative? R-CO-NH2
amide
43
Carboxylic acids react by ______ _______ _______, where one nucleophile replaces another on the acyl (C=O) carbon atom.
nucleophilic acyl substitution
44
What is the order of reactiveness (more reactive to less reactive) of the following acid derivatives: amide, ester, acid chloride, carboxylic acid?
acid chloride, ester, amide, carboxylic acid
45
What are the best reagents for converting carboxylic acids to acid chlorides?
SOCl2 and COCl2
46
Reduction of a carboxylic acid with an alcohol under acidic conditions produces what?
ester
47
What is the formula of diazomethane?
CH2N2
48
How are carboxylic acids converted to their methyl esters?
adding CH2N2
49
What is the structure of methyl ester?
R-CO-O-CH3
50
What are the properties of diazomethane?
toxic, explosive, yellow gas
51
Which is more efficient, Fischer esterification or esterification of an acyl chloride?
esterification of an acyl chloride
52
The initial reaction of a carboxylic acid with an amine gives an ________ __________ ________.
ammonium carboxylate salt
53
What reacts with acid chlorides to give amides?
ammonia and amines
54
What reduces carboxylic acids to primary alcohols?
LiAlH4
55
BH3 * THF will not reduce a _____
ketone
56
What does BH3 * THF reduce carboxylic acids to?
primary alcohols
57
Lithium aluminum tri(tert-butoxy)hydride is a _______ reducing agent than lithium aluminum hydride.
weaker
58
Why does lithium aluminum tri(tert-butoxy)hydride reduce acid chlorides?
they are strongly activated toward nucleophilic addition of a hydride ion

Organic Chemistry II (8 decks)

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