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Organic Chemistry II > Chapter 12 - Alcohols > Flashcards

Chapter 12 - Alcohols Flashcards

1
Q

What is an alcohol?

A

Alcohols possess a hydroxyl group (-OH)

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2
Q

What is a phenol?

A

Phenols possess a hydroxyl group directly attached to an aromatic ring

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3
Q

Alcohol and phenol classification: Nomenclature procedure (5 steps)

A
  1. Identify the parent chain, include -OH even if it makes the chain shorter
  2. Identify, name, and alphabetize substituents
  3. Assign locants and prefixes to each substituent, give the lowest locant to the -OH
  4. Place -OH locant just before -ol suffix in parent chain
  5. Address stereochemistry
    * Cyclic alcohols: -OH is assumed to be on carbon 1, locant is assumed
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4
Q

Common alcohol names (3)

A

Iso-propyl alcohol, turt-butyl alcohol, benzyl alcohol

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5
Q

Properties of alcohols (4)

A
  1. Raises boiling point (intermolecular forces)
  2. Miscible in water if less than eight carbons
  3. More acidic than amines and alkanes (resonance, induction, solvation)
  4. Deprotonated by NaH or Na with K/Li
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6
Q

Preparation of alcohols: SN2
(Starting materials, reaction conditions, major products)

A

Starting material: Primary alkyl halide
Reaction conditions: NaOH
Products: Primary alcohol

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7
Q

Preparation of alcohols: SN1
(Starting materials, reaction conditions, major products)

A

Starting material: Tertiary alkyl halide
Reaction conditions: H2O
Products: Tertiary alcohol

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8
Q

Preparation of alcohols: Addition (3 types)
(Starting materials, reaction conditions, major products)

A
  1. Starting material: Alkene
    Reaction conditions: Dilute H2SO4
    Products: Secondary alcohol
    *Rearrangements
  2. Starting material: Alkene
    Reaction conditions: 1) Hg(OAc), H2O | 2) NaBH4
    Products: Secondary alcohol
  3. Starting material: Alkene
    Reaction conditions: 1) BH3-THF | 2) H2O2, NaOH
    Products: Primary alcohol
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9
Q

Preparation of alcohols: Reduction (3 types)
(Starting materials, reaction conditions, major products)

A
  1. Starting material: Carbonyls, alkenes, alkynes
    Reaction conditions: H2, Pt or Pd or Ni
    Products: Secondary alcohol
    Will reduce all alkenes and alkynes
  2. Starting material: Ketones, aldehydes, imines
    Reaction conditions: NaBH4, EtOH or MeOH or H2O
    Products: Secondary alcohol
    Will only reduce carbonyl
  3. Starting material: Ketones, aldehydes, imines, esters, carboxylic acids
    Reaction conditions: 1) LAH | 2) H2O
    Products: primary alcohol
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10
Q

Draw a mechanism for alcohol formation via reduction with BH4

A

Seriously, draw it.

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11
Q

Draw a mechanism for alcohol formation via reduction with LAH

A

No skipping!

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12
Q

Calculating carbon oxidation number (2 steps)

A
  1. Give electrons heterolytically to more electronegative atom
  2. Oxidation # = Valence - # of electrons on the carbon
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13
Q

What does an increase in an atom’s oxidation number mean? What about a decrease?

A

Increase in an atom’s oxidation number means the atom has been oxidized. A decrease means the atom has been reduced.

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14
Q

Why won’t tertiary alcohols undergo oxidation?

A

There are no hydrogens to remove

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15
Q

How do you name a diol? IUPAC? Common name?

A

Name using “diol” suffix and give a locant for each hydroxyl for IUPAC

Common names use “glycol”

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16
Q

How do you prepare a diol?

A

Reduce a di-carbonyl or syn/anti dihydroxylate an alkene

17
Q

Draw a generic Grignard reagent

A

R-Mg-X

18
Q

Why must water be avoided in the presence of a Grignard reagent?

A

The Mg-C bond has high ionic character that makes the carbon act as a nucleophile and/or a base. As a base, it will react with the water instead of completing the desired reaction.

19
Q

How does a Grignard reagent react in the presence of a carbonyl? What about an ester?

A

The Grignard reagent will form an -OH (reduce the carbonyl) and form a new C-C bond (adds on whatever alkyl group is attached to the reagent).

The reagent will react twice with an ester and add two R groups

20
Q

Draw the mechanism for a Grignard reaction

A

Dude, you know whichever mechanism you don’t practice will be on the test.

21
Q

What are the starting materials for a Grignard reaction? Reaction conditions? Product?

A

Grignard reagents react with carbonyls to produce alcohols.

Reaction conditions: 1) RMgBr | 2) H2O

22
Q

What is the name of the synthesis strategy used to overcome reaction incompatibilities?

A

Protection/deprotection strategy

23
Q

Explain the general steps (3) of a protection/deprotection strategy and name reagents involved in each step

A

Protect the carbonyl/oxygen by using TMS-Cl, Et3N. Perform the Grignard reaction using 1) RMGBr | 2) H2O.
Deprotect by using TBAF

24
Q

Will Grignard reactions work on -OH groups?

A

No, the -OH will quench the reagent

25
Q

Reaction conditions for the halogenation of alcohols: SN1

A

H-Br
[G]
* Tertiary alcohols

26
Q

Reaction conditions for the halogenation of alcohols: SN2

A

H-Br
[G]
* Primary alcohols

27
Q

Reaction conditions (2) for the halogenation of alcohols: Chlorination

A

HCl, ZnCl2
[CCC]
* Primary alcohols

SOCl2, Pyridine
[L]
* Primary/secondary alcohols

28
Q

Reaction conditions for the halogenation of alcohols: Bromination

A

PBr3
[BBB]
* Primary/secondary alcohols

29
Q

Reaction conditions for the halogenation of alcohols: Any halogen

A

TsCl, Pyridine
[C]
* Primary/secondary alcohols

30
Q

Reaction conditions for the elimination of alcohols: E1

A

H2SO4, heat
[F]
* Tertiary alcohols

31
Q

Reaction conditions for the elimination of alcohols: E2

A

TsCl, Pyridine, NaOEt
[C]
* Tertiary alcohols

32
Q

Reaction conditions (2) for the oxidation of alcohols: Primary alcohols

A

Na2Cr2O7, H2SO4, H2O
[I]
* Will oxidize all the way to a carboxylic acid

PCC, CH2Cl2
[VV]
* Will stop at an aldehyde

33
Q

Reaction conditions for the oxidation of alcohols: Secondary alcohols

A

PCC, CH2Cl2
[VV]

34
Q

Reaction conditions for the oxidation of alcohols: Tertiary alcohols

A

Sorry, this one’s a trick. Tertiary alcohols can’t be reduced - they don’t have any hydrogens.

35
Q

Draw a general oxidation of a secondary alcohol using chromic acid.

A

Keep practicing :)

36
Q

What reaction conditions will cause the oxidation of an alcohol to a carbonyl?

A

PCC, DCM
[VV]

37
Q

Name a biological redox reagent

A

NAD+/NADH

38
Q

Phenols oxidize to form ___________

A

Benzoquinones

Organic Chemistry II (1 decks)

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