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Premed95 > Chem3 - Oxygen Rxns > Flashcards

Chem3 - Oxygen Rxns Flashcards

1
Q

Carboxylic acids typically do NOT undergo

A

nucleophilic addition

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2
Q

what is a nucleophile?

A

attacks, donates electrons (lewis base), usually strong baseshigher electronegativity=decreased nucleophilicity

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3
Q

what is the leaving group?

A

what is kicked off when the nucleophile attacks, definied by its stability alone or in solution. usually a weaker base

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4
Q

alcohol

A

R-OH, H bonds, increases BP, can act as a nucleophile and a leaving group

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5
Q

what is the function of a tosylate?

A

has a benzne ring, usually used to protect alcohols

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6
Q

what is a mesylate?

A

usually used as a protecting group, has no benzene ring

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7
Q

ether

A

R-O-R,can H bond but is relatively non reactive

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8
Q

what is an electrophile?

A

gets attacked, usually with + charge.carbonyls common

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9
Q

aldehydes and ketones being attacked can produce a ____ mixture

A

racemic

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10
Q

what does stereoselective mean?

A

prefers R or S

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11
Q

what does stereospecific mean?

A

100% or 0% of an isomer formed

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12
Q

acid halide+RCOOH=

A

anyhdride

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13
Q

acid halide+water=

A

COOH

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14
Q

acid halide+ROH=

A

ester

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15
Q

acid halide+RNH2=

A

amide

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16
Q

what is the leaving group on an anhydride?

A

a carboxylate (R-COO-)

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17
Q

what is transesterification?

A

one alkoxy group is substituted for another

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18
Q

what is a lactone?

A

formed by intramolecular cyclization

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19
Q

amides are the least reactive carbonyl, T/F

A

T

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20
Q

what is a lactam?

A

cyclic amide

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21
Q

do aldehydes and ketones have a leaving group?

A

no

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22
Q

what does the kinetic enolate form during tautomerization?

A

least substituted alkene with lower Ea

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23
Q

what does the thermodynamic enolate form?

A

most substituted alkene

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24
Q

what is the produce of an aldhyde and a ketone reacting?

A

a hemiacetal

25
Q

imine=? enamine=?

A

C=N-RHC=C-NRR

26
Q

NABH4 and LiAH4(LAH) are

A

reducing agents that reduce ketones and aldehydesonly LAH reduces COOH, esters, & acetates

27
Q

cyanohydrin?

A

CN-, attacks carbonyl and produces a COOH when exposed to acid+water

28
Q

how many bonds can P form?

29
Q

what is oxidation?

A

increase in H bonds to O or X, loss of CH bonds

30
Q

what is reduction?

A

increase in H bonds or R groups, loss of O or X bonds

31
Q

what is Oxygens typical oxidation state?

32
Q

can you oxidize a tertiary alcohol?

33
Q

oxidizing agents usually have many

A

O atomsK2CrO7, KmNO4, PCC

34
Q

reducing agents usually have many

A

H atomsLAH, NaBH4,

35
Q

NaBH4 reduces only

A

ketones and aldehydes

36
Q

what could you use to oxidize OH down to COOH

A

KmNO4, CrO4-, Cr2O4-

37
Q

what does PCC do?

A

oxidize primary alcohols to aldehydes and secondary alcohols to ketones

38
Q

what is the basic mechanism of an aldol condensation?

A

alpha carbon attacks another carbonyl

39
Q

what is the main functional group in an aldose?

40
Q

what is the main functional group in a ketose?

41
Q

how do you name carbohydrates?

A

in a fisher projection, start numbering at carbonyl, if highest # carbon’s OH is on right it is (D) otherwise it is (L)

42
Q

what is the anomeric carbon

A

found at new chiral center where the carbonyl was attacked

43
Q

what is the alpha anomer?

A

when the OH and methoxy groups are opposite to eachother

44
Q

what is the beta anomer?

A

when the alpha and methoxy groups are on the same side

45
Q

furanose?

A

5 member ring

46
Q

pyranose?

A

6 member carbohydrate ring with O

47
Q

what is the structure of sucrose?

A

alpha 1,1 link of glucose and fructose

48
Q

maltose structure

A

alpha 1-4 of 2 glucose

49
Q

lactose structure

A

beta 1-4 link of galactose and glucose

50
Q

cellulose structure

A

beta 1-4 link of glucoses

51
Q

amylose structure

A

alpha 1-4 link of glucose

52
Q

glycogen structure

A

alpha 1-4 links of glucose with alpha 1-6 BRANCH POINTS

53
Q

what are the reagents/products of the gabriel synthesis?

A

uses potassium phtalimide

54
Q

what is the strecker synthesis?

A

used to make amino acids

55
Q

what does amphipathic mean?

A

hydrophobic with hydrophilic end

56
Q

structure of triglyceride

A

3 fatty acids+ glycerol

57
Q

what is an unsaturated fatty acids?

A

has 1 or more double bonds

58
Q

grignard reagents create new ___ bonds

A

carbon-carbon

59
Q

two cysteines combine to form a

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