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exam 3 Flashcards

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1
Q

What are some oxidizing agents?

A

PCC, DMP, Swern, KMno4, H2CrO7

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2
Q

How do we oxidize a primary alcohol to an aldehyde?

A

With a weak oxidant, like PCC, DMP, or Swern

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3
Q

How do we oxidize a primary alcohol to a carboxylic acid?

A

With a strong oxidant, like KMnO4 or Cr2O7

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4
Q

What happens when we oxidize a secondary alcohol with any oxidant

A

We get a ketone

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5
Q

How do we generate an aryl ketone (ketone with benzene as an R group)

A

Friedel Crafts acylation

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6
Q

What are the reagents of alkyne hydration?

A

H2O and H2SO4

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7
Q

What is the product of alkyne hydration

A

A ketone, via keto-enol tautomerization

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8
Q

What is one way to generate aldehydes/ketones with an alkyne as a starting product?

A

Hydroboration oxidation

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9
Q

What are the reagents for hydroboration oxidation?

A

1) BH3, THF
2) NaOH, H2O2

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10
Q

What is a way to generate carbonyls from alkenes

A

Ozonolysis

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11
Q

What are the reagents for ozonolysis?

A

1) O3
2) RED: DMS
2) OX: H2O2

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12
Q

How do we generate ketones/aldehydes from diols?

A

Oxidative cleavage

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13
Q

What are the reagents for oxidative cleavage of diols

A

NaIO4

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14
Q

Swern vs Jones

A

Jones (CrO3, H2SO4) oxidizes primary alcohols to carboxylic acids, but secondary alcohols to ketones

Swer oxidizes primary alcohols to aldehydes and secondary alcohols to ketones

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15
Q

How do we covert alkenes to alcohols

A

Hydroboration oxidation

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16
Q

Hydroboration oxidation alkenes vs alkynes

A

alkenes –> alcohols
alkynes –> aldehydes/ketones

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17
Q

Why is it useful to add cyanide to an aldehyde/ketone in synthesis

A

To make cyanohydrins (hydroxyl and nitrile on same carbon), which can be transformed into other functional groups, like COOH, esters, amines

Also extends carbon chain! useful for synthesis

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18
Q

How do we add HCN to aldehydes/ketones, and what is generated

A

Add cyanide, reduce carbonyl to alcohol and add CN

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19
Q

How do we generate a geminal diol (hydrate) from aldehydes/ketones

A

Hydration

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20
Q

How do we reduce aldehydes to PRIMARY alcohols

A

LiALH4 + w/u or NaBH4 + w/u

Catalytic hydrogenation also works, but stereospecific (syn)

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21
Q

How do we reduce ketones to SECONDARY alcohols

A

Grignard Addition

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22
Q

Aldehydes get reduced to….

A

primary alcohols

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23
Q

Ketones get reduced to….

A

secondary alcohols

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24
Q

What is an acetal

A

Geminal diether –> like geminal diol but with OR groups in place of OH

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25
How are acetals synthesized
Acid catalyzed addition of 2 eq ROH
26
How are acetals hydrolyzed, and what is generated
Acid/water, aldehyde/ketone generated
27
Rank carboxylic acid derivatives from most to least reactive
acid chlories, acid anhydrides, carboxylic acid, ester, amide, carboxylate
28
Rank carboxylic acid derivative from most to least acidic
acid chlorided, acid anhydrides, ester amides, nitriles
29
What is an imine
Organic compounds with C=N bonds
30
Usefulness of imines for synthesis
Vital intermediate for producing amines
31
How do we make imines
Reduce aldehydes/ketones
32
What are the reagents for imine synthesis
Primary amine and aldehyde/ketone + heat and H3O
33
What is an enamine
NR2 attached to alkene carbon (NR2-C=C)
34
How do we make alkanes from aldehydes/ketones
Wolff-Kishner or clemmensen reduction
35
What are the reagents for Wolff-Kischner
N2H4 (H2N-N2H) and strong base (OH-) at high temp (>150)
36
What are the reagents for clemmensen reaction
ZNHg and Hcl
37
What is the purpose of Clemmensen and Wolff-Kischner reactions
Reduce aldehydes/ketones to alkanes
38
How do we reduce aldehydes/ketones to alkenes
Wittig Reaction
39
Usefulness of Wittig in organic synthesis
Generating new C-C double bond
40
What are the reagents for wittig
Ylide + aldehyde/ketone
41
How do we generate an ylide for wittig
1) Alkyl halide + PPh3 2) n-BuLi
42
How do we oxidize aldehydes to carboxylic acids
Strong oxidant! ex: Jones (CrO3 + H2SO4)
43
What is the pinacol rearrangement
1,2 diol into an aldehyde/ketone
44
What are the reagents for pinacol rearrangement
Acid
45
How do we generate a carboxylic acid from a nitrile
Nitrile hydrolysis
46
How do we generate carboxylic acids while simultaneously extending carbon chain by 1
Grignard Addition to CO2
47
What are the reagents for Grignard addition to generate a carboxylic acid
Grignard reagent + CO2
48
How do we generate a carboxylic acid from a methyl ketone
Haloform reaction
49
What is a methyl ketone
Carbonyl attached to a methyl group and an R chain
50
What are the reagents for the haloform reaction?
1.) NaOH, X2 2.) acidic w/u
51
What are some ways to make esters?
Fischer esterification or alkylation
52
How do we make an ester from a carboxylic acid
Fischer esterification OR alkylation
53
What are the reagents for fischer esterification
(COOH) + ROH + Acid
54
Mechanism of fiscer esterification
PADPED
55
When to use alkylation instead of fischer esterification to make an ester?
When the substrate is acid sensitive, if substrate is tertiary alcohol
56
What are the reagents for alkylation
Diazomethane (CH2N2) OR alkyl halides + base
57
How do we make acid chlorides
Acid chloride synthesis
58
What are the reagents + substrate for acid chloride synthesis
Substrate: carboxylic acid Reagents: SOCl2 or PCl2
59
What are the reagents /substrate for anhydride synthesis?
2 carboxylic acids + dehydrating agent (P2O5)
60
How do we generate a primary alcohol from a carboxylic acid
Hydride reduction
61
What are the reagents for hydride reduction?
(COOH) + LIAlH4, H2SO4
62
How do we reduce carbonic acid derivatives, beta keto acids derivatives and malonic acid derivatives?
Decarboxylation
63
Whaat are the reagents for decarboxylation
Acid, maybe heat
64
How do we generate an ester from a ketone
Baeyer Villiger Oxidation
65
What are the reagents for Baeyer Villiger Oxidation
(Ketone) + Peracid
66
What is Baeyer Villiger oxidation
Way to generate esters from ketones
67
How do we hydrolyze esters to carboxylic acids?
Saponification
68
What is saponification
Hydrolysis of esters to caarboxylic acids
69
What are the reagents for saponification of esters
1) [OH]- 2) acidic w/u
70
How do we generate carboxylic acids from amides
Amide hydrolysis
71
What are the reagents for hydrolysis of amides?
strong acid or base
72
How do we generate carboxylic acids from acid chlorides or anhydrides
Hydrolysis
73
What are the reagents for acid chloride / anhydride hydrolysis
Water
74
How do we make amides?
React acid chloride + (2) ammonia
75
What is second way to generate anhydrides
React acid chlorides with carboxylate salts
76
How do we make primary alcohols from esters
Reduction with LAH
77
How do we generate amines from amides?
Reduction with LAH
78
How do we generate amines from nitriles
Reductions with LAH
79
How do we generate aldehydes from acid chlorides
Rosemund Reduction
80
What is the rosemund reduction
Reaction wherein an acid chloride is reduced to an aldehyde
81
What are the reagents for the rosemund reduction
H2 and quinoline OR LiAl(OtBu)H, -80
82
How do we generate a secondary/tertiary alcohol from an ester
Grignard reduction
83
What are the reagents for grignard reduction of esters
1) 2 MgBr 2) acid
84
How do we generate a ketone from an acid chloride
Grignard reduction
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