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Chem 31 > Module 10: Carbonyl Chemistry > Flashcards

Module 10: Carbonyl Chemistry Flashcards

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
Q

these cannot undergo substitution because they have no leaving group bonded to the newly formed sp3 hybridized carbon

A

aldehydes and ketones

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26
Q

_______________ in sugars are formed by cyclization of hydroxy aldehydes.

A

hemiacetals

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27
Q

degree of all carbonyl carbon bonds?

A

120 degrees

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28
Q

ketones are less reactive making it more _____________ and more ____________

A

crowded, stable

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29
Q

The ________________________ makes the carbonyl carbon electrophilic

A

electronegative oxygen

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30
Q

An __________ can be hydrolyzed to an aldehyde or ketone by treatment with aqueous acid

A

acetal

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31
Q

it is the most common type of lipid

A

triacylglycerol

32
Q

these are strong organic acids

A

carboxylic acids

33
Q

Synthesis of acetals is reversible, and equilibrium often favors?

34
Q

these bonds are easily broken

35
Q

Aldehydes and ketones react with two equiv of alcohols to form?

36
Q

hybridization of carbonyl carbon?

A

sp2 hybridized

37
Q

a carbon atom bonded to one OH group and one OR group

A

hemiacetal

38
Q

Two equiv of alcohol are added to the?

A

carbonyl group

39
Q

Acid catalyzed:

A

p-toluenesulfonic acid (TsOH)

40
Q

these contains cyclic acetals or hemiacetals

A

carbohydrates

41
Q

Carbonyl compounds react with?

A

nucleophiles

42
Q

cyclic hemiacetals can be converted to?

43
Q

these are polyhydroxy aldehydes and ketones, or compounds that can be hydrolyzed to them

A

carbohydrates

44
Q

has two alkyl or aryl groups bonded to the carbonyl group

45
Q

geometry of carbonyl carbon?

A

trigonal planar

46
Q

compounds bonded to good leaving group are easily ___________

47
Q

nucleophiles attack __________

A

electrophiles

48
Q

the new ___________ of the hemiacetal can
occupy either the equatorial or axial position

49
Q

these are commonly referred to as sugars and starches

A

carbohydrates

50
Q

OR

A

alkoxy groups

51
Q

has at least one H atom bonded to the carbonyl group

52
Q

addition of alcohols - ?

A

acetal formation

53
Q

two broad classes of compounds that contain carbonyl group

A

aldehyde and ketone

54
Q

The presence or absence of a _____________ on the carbonyl carbon determines the type of reactions these compounds undergo.

A

leaving group

55
Q

these react with nucleophiles

A

carbonyl compounds

56
Q

carbonyl compounds that contain leaving groups undergo _____________________

A

nucleophilic substitution

57
Q

________________ are more reactive than _______________ towards nucleophilic attack for both steric and electronic reasons

A

aldehydes, ketones

58
Q

Carboxylic acids are strong organic acids and NH3 and amines are bases, so they undergo an acid–base reaction to form an?

A

ammonium salt

59
Q

Cyclic hemiacetals are formed by?

A

intramolecular cyclization of hydroxy aldehydes

60
Q

carbohydrates are polyhydroxy _________________ and __________________

A

aldehydes and ketones

61
Q

the new OH group of the hemiacetal can
occupy either the _____________ or __________________

A

equatorial, axial position

62
Q

cyclization forms a new __________________

A

stereogenic center

63
Q

The presence of the electronegative oxygen atom in the carbonyl group means that the bond is polarized, making the carbonyl carbon ____________________

A

electron deficient

64
Q

these undergo nucleophilic addition

A

aldehydes and ketones

65
Q

Aldehydes and ketones cannot undergo substitution because they have no leaving group bonded to the?

A

newly formed sp3 hybridized carbon

66
Q

aldehydes are more reactive, making it less __________ and less __________

A

crowded, stable

67
Q

An acetal can be hydrolyzed to an aldehyde or ketone by treatment with?

A

aqueous acid

68
Q

_______________________ containing five- and six- membered rings are stable compounds

A

cyclic hemiacetals

69
Q

Forms a hemiacetal with new stereogenic centers, resulting to an equal amount of?

A

enantiomers

70
Q

these react with two equiv of alcohols to form acetals

A

aldehydes and ketones

71
Q

An acetal can be hydrolyzed to an ____________ or _____________ by treatment with aqueous acid

A

aldehyde, ketone

72
Q

Synthesis of acetals is ________________, and equilibrium often favors reactants

A

reversible

73
Q

these are formed by intramolecular cyclization of hydroxy aldehydes; catalyzed by both acid and base.

A

cyclic hemiacetals

74
Q

In acetal, the carbonyl carbon from the aldehydes or ketone is now singly bonded to?

A

two OR (alkoxy) groups

75
Q

these can be converted to acetals by treatment with an alcohol and acid

A

cyclic hemiacetals

Chem 31 (22 decks)

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