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Chemistry > Oxygen Containing Reactions > Flashcards

Oxygen Containing Reactions Flashcards

1
Q

What are typical nucleophiles?

A

Alcohols, amines, hydrides

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2
Q

What are typical electrophiles?

A

Carbonyl carbon, phosphate groups

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3
Q

Only a ___ reactive molecule can form a ____ reactive molecule

A

More; less

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4
Q

Nucleophiles = Lewis ____

A

Bases

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5
Q

Alcohol attacks carbonyl C of COOH => ______

A

Ester

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6
Q

Alcohol attacks ketone/aldehyde => ______

A

Hemiketals/hemiacetals

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7
Q

Across a row, nucleophilicity _____

A

Increases

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8
Q

Good leaving group = _____ in solution

A

Stable

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9
Q

Atoms that leave as ____ = great LGs

A

Gases

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10
Q

_____ electron shells (_____ periods) => _____ charges => ______ LG and _____ nucleophile

A

More; higher; distribute; good LG; bad nucleophile

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11
Q

Weaker nucleophile can be an LG through _________ _______ reaction

A

Nucleophilic substitution

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12
Q

Best nucleophile = ______ _______

A

Strong base

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13
Q

Nitrogen = ______ nucleophilic than oxygen

A

More nucleophilic

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14
Q

Boiling point of OH goes _____ with molecular weight and ______ with branching

A

Up with MW; down with branching

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15
Q

OH has higher melting/boiling points than alkanes due to ______

A

Hydrogen bonding

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16
Q

OH typically acts as ____

A

Nucleophile

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17
Q

Alcohols = electron _____ group

A

Donating

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18
Q

Electron withdrawing groups make alcohols more ______

A

Acidic by drawing electron density away from acidic proton => increased partial positive charge

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19
Q

Electron donating groups make molecules more ____

A

Basic by stabilizing positive charge

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20
Q

Alkyl groups = electron ______ groups

A

Donating

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21
Q

Trend of alcohol acidity

A

Greater number of EDGs => weaker acid

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22
Q

Strongest to weakest alcohol acid:

A

Methyl > primary OH > secondary > tertiary

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23
Q

_____ OH has most _____ groups (which are _____)

A

Tertiary OH has most alkyl groups (EDGs) => makes it want to pick up proton (basic)

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24
Q

Hydrocarbons = electron _____

A

Electron donating

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25
Q

Alcohols = _____ LG b/c ______

A

Bad LG b/c reactive in solution

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26
Q

Alcohols become better LG by being _____ or ______

A

Protonated or converted to ester (sulfonate)

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27
Q

Formation of sulfonates = what type of reaction?

A

Nucleophilic substitution (OH = nucleophile)

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28
Q

Commonly used sulfonates = ____ and _____

A

Tosylates and mesylates

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29
Q

Sulfonates are useful for _____

A

Protection of alcohols (prevents OH from acting as acid or undergoing undesired reactions)

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30
Q

Ethers

A

R-O-R

  • Non-reactive
  • Usually shows up as solvent
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31
Q

Amines are ____ nucleohpile and _____ LG compared to O

A

Better nucleophile; worse LG

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32
Q

When N only appears w/ 3 bonds => ______

A

Draw in a lone pair

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33
Q

N acts as a nucleophile where lone pair attacks ______

A

Positive charge

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34
Q

Electron ______ groups on amine _____ basicity

A

Withdrawing; decrease

Donating; increase

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35
Q

Electrophiles usually have ______

A

Positive charge

Almost always carbonyls

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36
Q

Carbonyl has ______ stereochemistry

A

Planar => leaves space above and below to be attacked

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37
Q

Carbonyl C has a partial ______ charge

A

Positive

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38
Q

Carbonyl becomes more ______ by e- ______ groups

A

Stable; donating

Reactive; withdrawing

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39
Q

Most reactive carboxylic acid derivative = ______

A

Acyl chloride

- Cl pulls e- density

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40
Q

Least reactive COOH derivative = ______

A

Amide (O=CNH2)

- N donates e- density to C

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41
Q

If a carbonyl has a good LG => it will undergo ______

A

Nucleophilic substitution

- Cl or -OR groups leave

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42
Q

If a carbonyl does not have a good LG => it will undergo ______

A

Nucleophilic addition

- Aldehydes and ketones

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43
Q

Which is less reactive: ketone or aldehyde?

A

Ketone b/c it has an R group (EDG)

44
Q

Racemic mixture

A

Equal amounts of R and S

45
Q

Stereoselective

A

Prefers either R or S

- If bulk group that hinders approach of nucleophile from one side

46
Q

Stereospecific reaction

A

100% and/or 0% of unique stereoisomer is formed

47
Q

Lone pair on O in COOH amide, and ester ______ to carbonyl C

A

Donate e- density

48
Q

Carbonyls ______ OH as LG

A

Improve

49
Q

______ quality of COOH makes it vulnerable to ______

A

Planar; nucleophilic attack

50
Q

COOH derivatives can participate in

A

Nucleophilic substitution

51
Q

COOH make strong ____ bonds w/ each other => form ____, which increase ______

A

Hydrogen bonds; dimers; boiling point

52
Q

COOH = most soluble in ______ solvents

A

Nonpolar solvents b/c able to solvate in dimer form w/o H bonds of dimer being disrupted

53
Q

Electron ______ groups on alpha carbon stabilize conjugate base => ______ acidity of COOH/OH

A

Withdrawing; increase

54
Q

Carboxylic acid derivatives = formed by ______ ______

A

Nucleophilic substitution

55
Q

______ ______ = most reactive COOH derivative

A

Acid halide due to EWG nature of halide

56
Q

Most reactive COOH derivative to least:

A

Acyl halide > anhydride > ester > amide

57
Q

More stable the LG => more likely to undergo ______ ______

A

Nucleophilic substitution

58
Q

Anhydride

A

O=COC=O

- Ester w/ two carbonyls

59
Q

Anhydride has carboxylate anion LG = stabilized by ______

A

Resonance

60
Q

Hydrolysis of amides = only possible under ______ ______ ______

A

Extreme chemical conditions

- High temperature, strong acid

61
Q

Transesterification

A

Alcohols react with esters

- One alkoxy group (RO) is substituted for another in ester

62
Q

Intramolecular formation of ester = ______

A

Lactone

63
Q

Cyclic amides formed in intramolecular reactions = ______

A

Lactams

64
Q

Carbonyl carbon = substrate for ______

A

Acyl substitution

65
Q

Stronger base = stronger ______ = poor ______

A

Bond; LG

66
Q

Aldehydes and ketones undergo ______ reactions b/c ______

A

Addition reactions b/c they don’t have an LG

67
Q

Aldehydes and ketones exist at room temperature as ______-______ ______

A

Keto-enol tautomers

68
Q

Tautomerization = ______

A

Movement of single proton

  • Shift from carbonyl to alkene w/ alcohol
  • Deprotonation of alpha carbon + protonation of carbonyl oxygen
69
Q

Tautomers exist at ______, and are NOT a ______

A

Exist at equilibrium; are NOT a resonance

70
Q

Asymmetric ketons form two different enolates: ______ enolate and ______ enolate

A

Kinetic enolate (less substituted enolate) and thermodynamic enolate (more substituted double bond)

71
Q

Additional alcohol added to hemiacetal/hemiketal =>

A

Acetal/ketal

- OR group replaces OH group

72
Q

Acetals/ketals = good ______ ______

A

Protecting groups

73
Q

Aldehyde/ketons react w/ amines via ______ ______ to form ______ and ______

A

Nucleophilic addition => imines and enamines

  • Imine = similar to carbonyl (C=N)
  • Enamine = alkene w/ amine substituent
74
Q

Organometallic reagents (R-) and hydride ions (H-) react w/ aldehydes/ketones via ______ ______ to form ______

A

Nucleophilic addition => alcohols

- AKA Grignard reagents

75
Q

H- is hidden in hydride reagents like ______ and ______

A

NaBH4 and LiAlH4

76
Q

Cyanohydrin

A

NItrile (CN-) and OH attached to same carbon

77
Q

Phosphoric acid

A

Similar to carbonyl due to polar P=O bond

78
Q

When heated, phosphoric acids => ______ ______

A

Phosphoric anhydrides

79
Q

Reduction = ______

A

Nucleophilic addition of hydride to carbonyl

  • Increase in bonds to H or R groups
  • Loss of bonds to O or halogen
80
Q

Oxidation = ______

A

Nucleophilic addition of O to carbon (EWG)

  • Increase in bonds to O or halogen
  • Loss of C-H bonds
81
Q

Oxidizing agents have several ______ ______

A

Several O atoms

- K2Cr2O7, PCC, O2

82
Q

Reducing agents have several ______ ______

A

Several H atoms

- LiAlH4, NaBH4, H2

83
Q

Oxidation of COOH to CO2 = ______

A

Decarboxylation

84
Q

Aldol condensation = ______

A

Carbonyl nucleophile attacks another carbonyl

- Due to alpha carbon (adjacent to carbonyl C) being a nucleophile

85
Q

Carbohydrates

A

Carbon chains w/ alcohol on each carbon except for one

- That one has aldehyde/ketone

86
Q

Aldoses

A

Carbohydrates w/ aldehydes

87
Q

Ketoses

A

Carbohydrates w/ ketones

88
Q

Human body can only assimilate ______ carbohydrates

A

D carbohydrates

89
Q

Carbohydrate w/ same structure except configuration around single chiral center

A

Epimers

90
Q

Anomeric carbon

A

Only C attached to 2 O’s

91
Q

Alpha anomer

A 
OH group (on C1) and methoxy group (on C6) are on opposite sides of carbon ring
- Alpha = opposite
92
Q

Beta anomer

A

C1 OH and C6 methoxy are on same sides of ring

93
Q

Alpha vs. beta mnemonic

A

AO that’s some BS

94
Q

5 membered ring

A

Furnaose

95
Q

6 membered ring

A

Pyranose

96
Q

Sucrose

A

1,1’ alpha linkage b/w glucose and fructose

- Only one that’s 1,1

97
Q

Maltose

A

Alpha 1,4’ b/w 2 glucose

98
Q

Lactose

A

Beta 1,4 galactosidic linkage b/ galactose and glucose

99
Q

Cellulose

A

Beta 1,4 b/w chain of glucose

100
Q

Amylose (starch)

A

Alpha 1,4 b/w chain of glucose

101
Q

Amylopectin + glycogen

A

Alpha 1,4 b/w branched chain of glucose w/ alpha 1,6 glucosidic linkages forming branches

102
Q

Gabriel synthesis of amino acids

A

N is protected in pthalimide => acts as nucleophile

103
Q

Strecker synthesis of amino acids

A

Aldehyde mixed w/ potassium cyanide and ammonium chloride

104
Q

Base catalyzed lipid breakdown

A

Saponification

105
Q

Saturated fatty acid

A

Higher melting points due to easy stacking (no kinks)

106
Q

Unsaturated fatty acid

A

Kinks => do not solidify easily => lower melting point

- All double bonds are cis

107
Q

Nucleic acid synthesis (phosphodiester bond formation)

A

O at 3’ C of one nucleotide attacks P at 5’ end of another

- OH acts as LG = nucleohpilic substitution reaction

Chemistry (4 decks)

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