Chapter #8 Flashcards

(43 cards)

1
Q

are carboxylic acids or alcohols more acidic?

A

carboxylic acids: they have more resonance (two oxygen atoms) that stabilizes the negative charge when the Hydrogen leaves.

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2
Q

for the basic common named carboxylic acids, how many carbons do formic acid, acetic acid, and propionic acid have respectively?

A

1
2
3

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3
Q

how many carbons does formaldehyde have?

A

1

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4
Q

how are cyclic carboxylic acids named?

A

name the cycloalkane and then add carboxylic acid as the suffix

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5
Q

how are salts of carboxylic acids named?

A

beginning with the cation followed by the name of the acid with -oate ending instead of -oic ending.

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6
Q

how do you name a molecule with 2 carboxylic acid groups?

A

“-dioc acid” at the end of the alkane name.

Ex: butanedioc acid

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7
Q

what is the name of the structure with: 2 carboxylic acid groups and 2 carbons total

A

ethanedioic acid

oxalic acid

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8
Q

what is the name of the structure with: 2 carboxylic acid groups and 3 carbons total

A

propanedioic acid

malonic acid

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9
Q

what is the name of the structure with: 2 carboxylic acid groups and 4 carbons total

A

butanedioic acid

succinic acid

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10
Q

do alcohols or carboxylic acids have a higher boiling point and why?

A

carboxylic acids because they have a greater ability to H-bond (with the O-H group and the carbonyl O)

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11
Q

compare acidity of alcohols and carboxylic acids

A

A carboxylic acid is, therefore, a much stronger acid than the corresponding alcohol, because, when it loses its proton, a more stable ion results

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12
Q

compare the acidity of carboxylic acids and strong acids such as HCl

A

strong acids are stronger (pKa can be in the negatives while the pKa of carboxylic acids is around 4)

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13
Q

how can acidity be increased via substituents

A

more electron withdrawing groups increase acidity

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14
Q

is NO2 an electron withdrawing or donating group

A

electron withdrawing

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15
Q

is NH2 an electron withdrawing or donating group

A

electron donating

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16
Q

in terms of stabilization or destabilization, the _____ the substituent groups are to the carboxyl group, the ____ the effect.

A

closer

greater

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17
Q

compare the removal of carboxylic acid protons in monocarboxylic acids and dicarboxylic acids

A

first in dicarboxylic acid removed easier than mono but the second of dicarboxylic acid is harder to remove than mono

carboxylic acid on other side originally an electron withdrawing group but when the hydrogen leaves and leaves a negative charge then the ability for the other hydrogen to leave diminishes a lot

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18
Q

what is the most acidic hydrogen on a carboxylic acid

A

the hydroxyl hydrogen

19
Q

in a beta-carboxylic acid, is the alpha hydrogen more or less acidic than the hydroxyl hydrogens?

20
Q

what type of alcohol can be oxidized to carboxylic acids?

A

primary alcohols

secondary and tertiary cannot because they already have 2 bonds to carbons.

21
Q

discuss nucleophilic addition and subtitution

A

in addition, an OH is formed after addition to carbonyl

in substitution, a leaving group can leave so the carbonyl reforms

22
Q

____ bases, which are the conjugate bases of strong acids, make good leaving groups

A

weak (stable)

23
Q

what conditions are necessary for the formation of an amide from a carboxylic acid and an amine?

A

basic or acidic

24
Q

what else is produced in the formation of an amide from a carboxylic acid and an amine?

A

water molecule

25
how are cyclic amides named (the ones that actually contain the N in the circle)
-lactam they are named based on the carbon attached to the N atom beta: beta carbon is attached to it.
26
what conditions are necessary for the formation of an ester from a carboxylic acid and an alcohol?
acidic conditions
27
what is the name of the reaction that forms an ester from carboxylic acid and alcohol?
esterification
28
what is one method to increase the rate of esterification reaction between an alcohol and carboxylic acid
do it in an acidic solution so the carbonyl oxygen is protonated. This increases the polarity of the bond
29
how are anhydrides formed via carboxylic acids
formed via the reaction of two carboxylic acids together | condensation reaction
30
what can be used to reduce carboxylic acids?
``` LiAlH4 NaBH4 cannot (too soft) ```
31
Can NaBH4 reduce carboxylic acids?
Na B, it's too soft! Cant reduce them at all, not even to aldehydes
32
describe decarboxylation
loss of carboxyl group as CO2
33
what is a soap and how is it formed?
salt of carboxylic acid | formed via addition of hydroxide
34
how is a cyclic anhydride named?
same as normal just with anhydride at the end
35
Can NaBH4 reduce carboxylic acids to aldehydes?
no
36
the ____ the anions, the more stable they are
larger
37
what 3 factors determine how good an acid is?
stability of the base: size (larger the better acid), EN (more EN the better acid), and resonance of the conjugate base (stabilize charge)
38
decarboxylation MUST occur via a _____ intermediate
6 membered ring (which includes the hypothetical bond between carbonyl and carboxylic acid H)
39
what types of compounds are involved in decarboxylation reactions?
beta keto acids and 1,3-dicarboxylic acids
40
can carboxylic acids be reduced to alkenes in one step?
no, it uses 2 steps.
41
discuss micelles
in polar solution, assemble with polar heads on outside and nonpolar fatty acid chain on interior.
42
why is the hydroxy hydrogen more acidic then the alpha hydrogen in carboxylic acid?
because once removed, the negative charge from the hydroxy H leaving can be shared among 2 oxygens.
43
describe how acidic and basic solutions make acyl substitution reactions favored?
basic: nucleophile better acid: electrophile better