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Chemistry > Oxygen Containing Reactions > Flashcards

Oxygen Containing Reactions Flashcards

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1
Q

Nucleophile

A

Donates e- , lewis base, low electronegativity
RhH2C > RHN- > RO-
ex. -OH and -NH to attack carbonyl

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2
Q

Leaving grp

A

Portion of molecule that leaves when carbonyl attacked

Good leaving groups: atoms in higher periods, gases, weak nucleophile/weak base

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3
Q

Leaving Grp vs. Nucleophilicity

A

Leaving grp quality ————————————>

CH3- NH2- OR- OH- NH3 RCOO- H2O

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4
Q

Alcohols

A

Name ends in -ol, name takes precedence unless carbonyl present, increases BP

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5
Q

Rxns of Alcohols

A

As nucleophiles: (O donates e-)
As acids: (strongest) methyl> 1° > 2° >3° (weakest)
As leaving grp: Nucleophilic Substitution, -OH as nucleophile (ex. Tosylates and Mesylates for -OH protection)

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6
Q

Alcohol -> Alkyl halide

A

CH3-CH-OH + H-Cl ->Cl- + CH3-CH-OH2+ ->Cl-CH2-CH3 + H20
O donates e- and take H from H-Cl
H2O leaves and Cl- takes its place

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7
Q

Synthesis of Toslate and Mesylate

A

H-OR acts as nucleophile and causes Cl- to leave to become H-Cl

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8
Q

Ether Rxns

A

Common solvent (relatively non-reactive), participates in substitution rxn or cleavage if a reactant

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9
Q

Cleavage of Ether

A

R-O-R’ + H-Br -> R-OH + R-Br

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10
Q

Nitrogen Rxns

A

Better nucleophile/worse leaving grp than O

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11
Q

Nitrogen as Nucleophile

A

Lone pair e- attacks + charge
Nucleophilic Additon: Amine + Aldehyde/ketone
Nucleophilic substitution: Amine + carboxylic acid

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12
Q

Nitrogen as Base

A

N takes on 4th bond becoming + charged

Ammonia/amines donate e- (acts as base)

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13
Q

Electrophiles and Rxns

A

Most have carbonyls, planar chemistry aids in decreasing steric hindrance, C with δ+
w/ leaving group: nucleophilic substitution rxn (acyl chlorides, esters, amides)
w/o leaving group: nucleophilic addition rxn (ketones, aldehydes)

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14
Q

Reactivity of Carbonyls

A

Least -> Amide - Carboxylic acid - Acid Anhdride/Ester - Ketone/Aldehyde - Acid Halide -> Most reactive

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15
Q

Carboxylic Acid Rxns

A

Via Substitution rxns (either acts as acid and gives up H or has H20 as leaving group)
Carb. acids w/ 4 or fewer C are soluble in H20 (10+ not)

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16
Q

Common Carboxylic Acid Derivatives

A

O
|| Carboxylic Acid
R-C-OH

 O
  ||                      Formic Acid  H-C-OH

     O
      ||                  Acetic Acid  3HC-C-OH

 O
 ||                      Benzoic Acid  Ar-C-OH
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17
Q

Reactiity of Carboxylic Acid Derivatives

A

Least -> Amide - Ester - Carb. Acid - Anhydride - Acid Halide -> Most

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18
Q

Esterification

A

Carboxylic acid + Alcohol -> H+ -> Ester + H20

Alcohol acts as nucleophile

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19
Q

Transesterification

A

Ester + Alcohol -> H+ -> New Ester + New Alcohol

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20
Q

Lactone Formation

A

Intramolecular esterification

21
Q

Ketone/Aldehyde Rxns

A

Via addition rxns
Very reactive because -H or -C don’t donate e- density
1. Nucleophile attacks carbonyl carbon
2.Carbon releases pi-bond e- to O
Acidic Conditions: O e- take H+ from acid, then Nuc attacks
Basic Condiions: Nuc attacks, O e- take H+ from H20

22
Q

Keto-enol tautomers

A

H hops to neighbor C, =O protonated
H O H OH H
| || | | |
R-C-C-C-H -> R-C=C-C-H
| | | |
H H H H

23
Q

Kinetic Enolate

A

Ketone in basic conditions, less substituted double bond, kinetically favored, less stable product

24
Q

Thermodynamic Enolate

A

Ketone in basic conditions, more substituted double bond, increases AE, more stable product

25
Q

Imine

A

Original amine has 0-1 R groups, C=N

26
Q

Enamine

A

Original amine has 2 R groups, C=C

27
Q

Grignard Synthesis of Alcohol

A

R-MgX + R-C=O -> R-3-C-O - + MgX -> R-3-C-OH + XMgOH

28
Q

Reduction Synthesis of Alcohol

A

H- + Ketone -> R-2-CH-O - -> R-2-CH-OH

29
Q

Oxidation

A

Increases bonds to O, loss of C-H bonds, decrease e- density

30
Q

Reduction

A

Increases bonds to H or R, decreases bonds to O, increase e- density

31
Q

Common Oxidizing Agents

A

K2Cr2O7 - 1° alcohol or aldehyde -> Carb. Acid
K2MnO4 - 1° alcohol or aldehyde -> Carb. Acid
H2CrO4 -1° alcohol or aldehyde -> Carb. Acid
O2
PCC - 1° alcohol -> aldehyde; 2° alcohol -> ketone

32
Q

Common Reducing Agents

A

LiAlH4: Carb. Acid or aldehyde -> 1° Alcohol
NaBH4: Aldehyde -> 1° Alcohol, Ketone -> 2° Alcohol
H2 + Pressure

33
Q

Decarboxylation

A

Carb. Acid -> CO2 (g), exothermic, hard to do

34
Q

Aldol Condensation

A

Carbonyl + Carbonyl

35
Q

Carbohydrates

A

C chain w/ alcohol on each carbon except for 1 w/ aldehyde or ketone (aldose/ketose)

36
Q

Carbohydrate Classification: Linear and Cyclic

A

D: highest -OH in Fischer projection on right
L: highest -OH in Fischer projection on left
α: -OH points opposite side of methoxy grp while cyclic
β: -OH points same side as methoxy grp while cyclic
5 member ring=furanose; 6 member ring=pyranose

37
Q

Di/polysaccharide fromation

A

Via dehydration (acetal formation)

38
Q

Common disaccharides

A

Sucrose: Glucose + Fructose, 1,2’ linkage
Maltose: Glucose + Glucose, α-1,4’ linkage
Lactose: Glucose + Lactose, β-1,4’ linkage
Cellulose: Chain of glucose, β-1,4’ linkage
Amylose: Chain of glucose, α-1,4 linkage
Amylopectin: branched glucose chain, α-1,4’ linkage w/ α-1,6’ branching
Glycogen: Branched glucose chain, α-1,4’ linkage w/ α-1,6’ branching

39
Q

Amino Acids

A

Contain amine and carboxylic acid

     O=C-OH
           |
      H-C-R
           |
          NH2
40
Q

Gabriel Synth

A

Amino acids synth de novo

41
Q

Strecher Synth

A

Amino acid from aldehyde + potassium cyanide + ammonium chloride

42
Q

Fatty Acids and Triglycerides

A

even numbered carbon chains w/ carboxylic acid at one end + glycerol + 3 fatty acid tails

43
Q

Lipogenesis

A

Fatty acids added on to glycerol to make triglyceride

44
Q

Lipolysis/Saponification

A

Removal of fatty acids from glycerol

45
Q

Saturated vs Unsaturated fatty acids

A

Saturated: no double bonds
Unsaturated: contains 1+ double bonds, decreased MP

46
Q

Nucleic Acids

A

P=O behaves like C=O

-OH on one nucleic acid creates anhydride with phosphate group of another (phosphodiester bond)

47
Q

Formation of Phosphodiester bond

A

Nucleophilic substitution rxn

-OH on nucleic acid attacks P of the other prod H20

48
Q

Hydrolysis of Phosphodiester bond

A

H2O added and -O attacks P releasing e- back to O of neighboring phosphate

Chemistry (7 decks)

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