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Organic Chemistry > Alcohols & Phenols > Flashcards

Alcohols & Phenols Flashcards

1
Q

Alcohols

A

Are compounds that possess a hydroxyl group (OH) & are characterized by names ending in “ol”

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2
Q

Nomenclature of alcohols

A
  1. Use the same 4 steps to name it as alkanes except it ends in “ol”
  2. Have to name it in a way that the longest chain contains the carbon atom that is directly connected to the OH
  3. The OH gets the higher priority over double bonds & other substituents groups
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3
Q

Phenol

A

Is a hydroxyl group attached to a phenyl

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4
Q

_______ is the parent’s name when a substituent is attached to it

A

Phenol

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5
Q

Alcohols have higher boiling points because of the __________

A

Hydrogen bonds

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6
Q

What are the two regions that alcohols have?

A
  1. Hydrophobic region
  2. Hydrophilic region
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7
Q

Hydrophobic region

A

Region that doesn’t interact with water

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8
Q

Hydrophilic region

A

Region that does interact with water through hydrogen bonds

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9
Q

Methanol is ________ in water but butanol is soluble

A

Miscible

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10
Q

Miscible

A

Can be mixed in a solvent in any proportion

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11
Q

Soluble

A

Means that only a certain volume of solute will dissolve in specified amount of solvent at room temp

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12
Q

As the size of the hydrophobic region increases __________ in water decreases

A

Solubility

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13
Q

Alcohols with more than eight carbons (like nonanol & decanol) are considered to be ________ in water

A

Insoluble

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14
Q

The conjugated base of alcohols are called what?

A

Alkoxide ion

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15
Q

pKa for most alcohols is between what?

A

15-18

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16
Q

What are the two common ways to deprotonate an alcohol to form an alkoxide ion?

A
  1. A strong base like sodium hydride because H- deprotonates the alcohol to generate H2
  2. Using Li, Na, or K to react with the alcohol to liberate H2
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17
Q

What are the factors affecting the acidity of alcohols & phenols?

A
  1. Resonance
  2. Induction
  3. Solvation effect
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18
Q

Resonance

A

If a compound has resonance its more acidic

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19
Q

When phenol is deprotonated, the conjugated base is stabilized by ______ so it’s pretty acidic

A

Resonance

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20
Q

Induction

A

Alcohols that have induction are more acidic by the electron withdrawing affect

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21
Q

Solvation effect

A

Straight chain alcohol more acidic than branched alcohols due to steric affect

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22
Q

Alcohols can be prepared by substitution reaction where a leaving group is replaced by __________

A

Hydroxyl group

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23
Q

_________, _________, & __________ adds an OH in an addition reaction

A

Acid catalyzed hydration, oxymercuration demurcuration & hydroboration

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24
Q

Converting ketone (or aldehyde) to an alcohol is a __________

A

Reduction (requires a reducing agent)

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25
Q

What are the 3 reducing reagents?

A
  1. H2/Pt, Pd, or Ni
  2. Sodium borohydride (NaBH4) & solvent EtOH, MeOH, or H2O
  3. Lithium aluminum hydride (LAH or LiAlH4) & H2O
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26
Q

Describe the mechanism of a reduction of a ketone or aldehyde with NaBH

A
  1. Nucleophilic attack
  2. Proton transfer
27
Q

Describe the mechanism of a reduction of a ketone or aldehyde with LAH

A
  1. Nucleophilic attack
  2. Proton transfer
28
Q

______ & ______ is better than hydrogenation because they can selectively reduce a carbonyl group

A

NaBH4 & LAH

29
Q

____ is more reactive so ______ is less selective & will react with carboxylic acid or an ester to produce an alcohol

A

LAH (NaBH4 wont)

30
Q

Describe the mechanism of a reduction of an ester with LAH

A
  1. Nucleophilic attack
  2. Loss of leaving group
  3. Nucleophilic attack
  4. Proton transfer
31
Q

Diols

A

Compounds with two hydroxyl groups

32
Q

How do you name diols?

A
  1. The position of both hydroxyl groups are identified with the numbers of places before the parent
  2. The suffix “diol” added at the end
33
Q

Diols can be made from ______ via reducing agents

34
Q

Diols can also be made by __________ of an alkene

A

Dihydroxylation (Ani or Syn)

35
Q

Grignard Reagent

A

Formed by the reaction between an alkyl halide & magnesium

36
Q

Carbon is more electronegative than _____ where their bond can be seen as ionic bond

37
Q

Grignard reagents are carbon _______ that can attack carbonyl group of ketones & aldehydes

A

Nucleophiles

38
Q

Describe the mechanism of Grignard reagent with a ketone or aldehyde

A
  1. Nucleophilic attack
  2. Proton transfer
  3. Product is an alcohol
39
Q

Grignard reagents also react with esters to make alcohols by adding two _____ groups

A

R (alkyl groups)

40
Q

Describe the mechanism of a Grignard reagent with an ester

A
  1. Nucleophilic attack
  2. Loss of leaving group
  3. Nucleophilic attack
  4. Proton transfer
41
Q

Its not possible to make a Grignard reagent without _______

A

Protecting

42
Q

What are the 3 steps in protecting to make a Grignard reagent?

A
  1. Protect the hydroxyl group by removing & converting the hydroxyl group into a new group called a protecting group
  2. Form the Grignard reagent & perform the desired Grignard reaction
  3. Deprotect by converting the protecting group back into a hydroxyl group
43
Q

__________ is a protecting group

A

Trimethylsilyl ether (OTMS)

44
Q

Trimethylsilyl is formed by the reaction between an ______ & ________

A

Alcohol & Trimethylsilyl chloride (TMSCl)

45
Q

After Grignard reaction is made the ________ group is removed easily with either H3O+ or fluoride ion such as tetrabutylammonium fluoride (TBAF)

A

Trimethylsilyl

46
Q

_________ are prepared industrially via multistep process involving the formation & oxidation of cumene

47
Q

To replace an OH with Cl have to use what?

A

ZnCl2 (As a catalyst) (It makes the OH a better leaving group)

48
Q

_________ alcohols will react in an SN2 reaction

A

Primary alcohol

49
Q

Primary & Secondary alcohol will react with _____ or ______ via SN2 reaction

A

SOCl2 or PBr3

50
Q

In an E1 an OH can be protonated but in an E2 it can be turn into _______ followed by a strong base

51
Q

Primary alcohol has two protons at the alpha position (carbon with the OH) so therefore can be oxidized twice where the 1st oxidation produces ______ & 2nd oxidization produces ________

A

Aldehyde, Carboxylic Acid

52
Q

Secondary alcohol only has one proton at the alpha position so they can only be oxidized once forming a _________

53
Q

________ alcohol don’t have any protons so can’t be oxidized

54
Q

_________ is the most common oxidizing reagent where it is formed from sodium dichromate (Na2Cr2O7) or chromium trioxide (CrO3) in an aqueous acidic solution

A

Chromatic Acid H2CrO4

55
Q

When a primary alcohol is oxidized with chromic acid a __________ is obtained

A

Carboxylic Acid

56
Q

When pyridinium chlorochromate (PCC) is used as oxidizing reagent an ________ is the final product

57
Q

______ is formed from the reaction between pyridine, chromium trioxide & hydrochloric acid

58
Q

__________ is the solvent used with PCC

A

Methylene Chloride (CH2Cl2)

59
Q

Phenol undergo oxidization to produce __________

A

Benzoquinone

60
Q

_________ such as benzoquinone can be converted to hydroquinones

61
Q

The ___________ rearrangement is a {3,3] sigmatropic rearrangement and is commonly observed for allylic vinylic ethers

A

Claisen rearrangement

62
Q

The Claisen rearrangement is also observed for _____________ ethers

A

Allylic aryl ethers

63
Q

During a Claisen rearrangement with aryl group (phenyl) & allylic group it is turned into a ketone and then tautomerized into an _________

64
Q

The reaction favors the tautomerization into the alcohol because it reforms the ___________ of the compound

Organic Chemistry (47 decks)

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