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Chem 31 > Module 10: Carbonyl Chemistry > Flashcards

Module 10: Carbonyl Chemistry Flashcards

(75 cards)

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1
Q

Forms a hemiacetal with new _________________________, resulting to an equal amount of enantiomers

A

stereogenic centers

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2
Q

The presence of the electronegative oxygen atom in the carbonyl group means that the bond is?

A

polarized

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3
Q

it forms a new stereogenic center

A

cyclization

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4
Q

these are the lipids that comprise animal fats and vegetable oils

A

triacylglycerols

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5
Q

Hemiacetals in sugars are formed by?

A

cyclization of hydroxy aldehydes

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6
Q

NH3 and amines are?

A

bases

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7
Q

Aldehydes are more reactive than ketones towards nucleophilic attack for both ________ and _____________ reasons

A

steric, electronic

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8
Q

RCOZ (Z = ?)

A

leaving group

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9
Q

this reaction converts the OH group that is part of the hemiacetal to an OR group

A

conversion of hemiacetals to acetals

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10
Q

in nucleophilic acyl substitution, nucleophilic attack forms an _________________________

A

sp3 hybridized intermediate

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11
Q

“uncrowded” carbon

A

Trigonal planar structure

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12
Q

two hydrolysis of esters

A

in aqueous acid and aqueous base

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13
Q

The electronegative oxygen makes the carbonyl carbon ________________

A

electrophilic

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14
Q

aldehydes and ketones undergo?

A

nucleophilic addition

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15
Q

Synthesis of acetals is?

A

reversible

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16
Q

The stability of RCOZ increases because of added __________________________

A

resonance stabilization

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17
Q

compounds that contain an electronegative atom bonded to the carbonyl group

A

acyl compounds

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18
Q

the better the leaving group Z, the ________________ RCOZ is

A

more reactive

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19
Q

this can be driven to the right by removing the water as it forms

A

equilibrium

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20
Q

Trigonal planar structure

A

“uncrowded” carbon

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21
Q

Esters are hydrolyzed with water in the presence of either an acid or a base to form?

A

carboxylic acids or carboxylate anions

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22
Q

Cyclic hemiacetals can be converted to acetals by treatment with an ____________ and ________

A

alcohol, acid

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23
Q

are hydrolyzed with water in the presence of either an acid or a base to form carboxylic acids or carboxylate anions

A

esters

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24
Q

examples of acyl compounds

A

carboxylic acids
acid chloride
ester
amide

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25
these cannot undergo substitution because they have no leaving group bonded to the newly formed sp3 hybridized carbon
aldehydes and ketones
26
_______________ in sugars are formed by cyclization of hydroxy aldehydes.
hemiacetals
27
degree of all carbonyl carbon bonds?
120 degrees
28
ketones are less reactive making it more _____________ and more ____________
crowded, stable
29
The ________________________ makes the carbonyl carbon electrophilic
electronegative oxygen
30
An __________ can be hydrolyzed to an aldehyde or ketone by treatment with aqueous acid
acetal
31
it is the most common type of lipid
triacylglycerol
32
these are strong organic acids
carboxylic acids
33
Synthesis of acetals is reversible, and equilibrium often favors?
reactants
34
these bonds are easily broken
π bonds
35
Aldehydes and ketones react with two equiv of alcohols to form?
acetals
36
hybridization of carbonyl carbon?
sp2 hybridized
37
a carbon atom bonded to one OH group and one OR group
hemiacetal
38
Two equiv of alcohol are added to the?
carbonyl group
39
Acid catalyzed:
p-toluenesulfonic acid (TsOH)
40
these contains cyclic acetals or hemiacetals
carbohydrates
41
Carbonyl compounds react with?
nucleophiles
42
cyclic hemiacetals can be converted to?
acetals
43
these are polyhydroxy aldehydes and ketones, or compounds that can be hydrolyzed to them
carbohydrates
44
has two alkyl or aryl groups bonded to the carbonyl group
ketone
45
geometry of carbonyl carbon?
trigonal planar
46
compounds bonded to good leaving group are easily ___________
cleaved
47
nucleophiles attack __________
electrophiles
48
the new ___________ of the hemiacetal can occupy either the equatorial or axial position
OH group
49
these are commonly referred to as sugars and starches
carbohydrates
50
OR
alkoxy groups
51
has at least one H atom bonded to the carbonyl group
aldehyde
52
addition of alcohols - ?
acetal formation
53
two broad classes of compounds that contain carbonyl group
aldehyde and ketone
54
The presence or absence of a _____________ on the carbonyl carbon determines the type of reactions these compounds undergo.
leaving group
55
these react with nucleophiles
carbonyl compounds
56
carbonyl compounds that contain leaving groups undergo _____________________
nucleophilic substitution
57
________________ are more reactive than _______________ towards nucleophilic attack for both steric and electronic reasons
aldehydes, ketones
58
Carboxylic acids are strong organic acids and NH3 and amines are bases, so they undergo an acid–base reaction to form an?
ammonium salt
59
Cyclic hemiacetals are formed by?
intramolecular cyclization of hydroxy aldehydes
60
carbohydrates are polyhydroxy _________________ and __________________
aldehydes and ketones
61
the new OH group of the hemiacetal can occupy either the _____________ or __________________
equatorial, axial position
62
cyclization forms a new __________________
stereogenic center
63
The presence of the electronegative oxygen atom in the carbonyl group means that the bond is polarized, making the carbonyl carbon ____________________
electron deficient
64
these undergo nucleophilic addition
aldehydes and ketones
65
Aldehydes and ketones cannot undergo substitution because they have no leaving group bonded to the?
newly formed sp3 hybridized carbon
66
aldehydes are more reactive, making it less __________ and less __________
crowded, stable
67
An acetal can be hydrolyzed to an aldehyde or ketone by treatment with?
aqueous acid
68
_______________________ containing five- and six- membered rings are stable compounds
cyclic hemiacetals
69
Forms a hemiacetal with new stereogenic centers, resulting to an equal amount of?
enantiomers
70
these react with two equiv of alcohols to form acetals
aldehydes and ketones
71
An acetal can be hydrolyzed to an ____________ or _____________ by treatment with aqueous acid
aldehyde, ketone
72
Synthesis of acetals is ________________, and equilibrium often favors reactants
reversible
73
these are formed by intramolecular cyclization of hydroxy aldehydes; catalyzed by both acid and base.
cyclic hemiacetals
74
In acetal, the carbonyl carbon from the aldehydes or ketone is now singly bonded to?
two OR (alkoxy) groups
75
these can be converted to acetals by treatment with an alcohol and acid
cyclic hemiacetals

Chem 31 (22 decks)

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