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O Chem 2 > Alcohols > Flashcards

Alcohols Flashcards

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1
Q

List 2 methods to synthesize alcohols

A

Using Grignard reagents

Reduction of carbonyl compounds

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2
Q

What are aldehydes reduced to?

A

Primary alcohols

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3
Q

What are ketones reduced to?

A

Secondary alcohols

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4
Q

What is a reagent used to reduce aldehydes and ketone and why?

A

Sodium borohydride because of it’s safety and use in either water and alcohol

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5
Q

Why do alcohols have higher boiling points than hydrocarbons of similar molecular weight?

A

Hydroxyl group will make alcohol susceptible to hydrogen bonding, unbounded electrons on the oxygen atom bond with hydrogen on another molecule

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6
Q

What primary alcohols are soluble in water?

A

Small alcohols, five carbons or fewer.

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7
Q

Why are small alcohols soluble in water?

A

Small alcohols participate in hydrogen bonding with water molecules

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8
Q

When an alcohol acts as a base, what type of ion does it become?

A

Oxonium ion

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9
Q

When an alcohol acts as an acid, what is the resulting ion?

A

Alkoxide ion

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10
Q

What will an increase in alkyl groups of alcohols have on acidity, pka and ka

A

Acidity decreases, pka increases, ka decreases

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11
Q

Why do substituents reduce alcohol acidity?

A

Stability of alkoxide ion is affected by solvation effects and electron withdrawing effects

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12
Q

Explain how acidity of alcohols with water is affected by the inductive effect/ electron withdrawal

A

Electron withdrawal delocalizes alkoxide ion negative charge, spreading it throughout the ion, adding to the ion stability, stabilizing product of deprotonation.( can be done with halide substituents)

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13
Q

Use biological oxidation to explain why methanol is poisonous

A

Methanol oxidizes to formaldehyde then Formic acid, which is more toxic than methanol

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14
Q

Use biological oxidation to explain what becomes of ethanol

A

Ethanol oxidizes to acetaldehyde, then acetic acid(a normal metabolite)

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15
Q

What does ethylene glycol oxidize to?

A

To oxalic acid, which is toxic

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16
Q

Name the reagents and products of an esterification reaction, without acyl chlorides

A

Reactants: alcohol + carboxylic acid

Catalyst: sulfuric acid

Products: ester + water

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17
Q

Using acyl chlorides, name the reagents and products of esterification

A

Reagents: alcohol + acid chloride

Product: ester + HCl

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18
Q

Name the reagents and products of Williamson ether synthesis

A

Reagents: alkoxide ion + primary halide or tosylatec strong base ( like NaH)

Products: ether

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19
Q

Why does William ether synthesis work best with primary alkyl halides?

A

It is an Sn2 displacement and so facilitates a back-side attack

20
Q

Name 4 reactions that can be used to convert alcohols into alkyl halides

A
  1. Reaction with hydrogen halides
  2. Reaction with phosphorous halides
  3. Reaction with Thionel Chloride
  4. Reaction with tosylate to form tosylate ester
21
Q

Why are tosylate and mesylates often used to convert alcohols to alkyl halides?

A

To avoid rearrangements to undesired products on secondary carbons

22
Q

What are used to prepare Lucas alcohol test?

A

ZnCl2 in concentrated HCl

23
Q

What are the results of each type of alcohol in Lucas test

A

Primary- reacts slowly or not at all

Secondary- reacts in 1-5 minutes

Tertiary- react in less than 1 minute

24
Q

What are the reagents for John’s alcohol test

A

Sodium dichromate in acid medium

25
Q

What are the results in John’s test for each type of alcohol?

A

Primary and secondary alcohols- gives positive reaction- orange dichromate ion and greenish blue chromic ion

Tertiary alcohols- do not react

26
Q

What are the results for the iodoform test?

A

Ethanol and secondary alcohols- positive test

Tertiary alcohols - no reaction

27
Q

What is the reagent of the iodoform alcohol test?

A

Triiodomethane- CHI3

28
Q

What type of alcohols are carboxylic acids and esters reduced to?

A

Primary alcohol

29
Q

What halogens can be used in Grignard reagents?

A

Cl, Br, or I but not F

30
Q

If an ester is used in Grignard reagents, what is the resulting alcohol?

A

Tertiary alcohol

31
Q

Why do larger-substituted alcohols decrease acidity of alcohols?

A

Bulky substituents groups prevent water from dissolving alcohols, making a sterically inaccessible alkoxide ions

32
Q

What kind of alcohol are carboxylic acids reduced to?

A

Primary alcohols

33
Q

What Grignard reagents?

A

These are alkyl-magnesium halides RMgX

34
Q

What are the reagents used to reduce an aldehyde or ketone?

A

Sodium borohydride, ethanol and hydronic ion

35
Q

What are the reagents used to reduce Carboxylic acids and esters

A

Lithium aluminum hydride, ether and a hydronium ion

36
Q

What 2 reactants can react with Grignard reactants to form a tertiary alcohol?

A

Ester and ketone

37
Q

Want happens when sodium borohydride, ethanol and H3O is added to dicyclohexyl ketone?

A

Dicyclohexyl ketone is reduced to dicyclohexylmethanol

38
Q

What catalyze biological oxidation?

A

Alcohol dehydrogenase

39
Q

What is the oxydizing of Biological oxidation?

A

Nicotineamide adenine dinucleotide

40
Q

What is treatment for ingestion of toxin forming alcohols (ethylene glycol and methanol)

A

Excess ethanol

41
Q

What is a catalyst to the Fischer esterification reaction?( alcohol and carboxylic acid)

A

Sulfuric acid

42
Q

How can phosphate esters be derived from alcohol?

A

Addition of an alcohol will be added to phosphoric acid to produce a phosphate ester and water

43
Q

In William ether synthesis, how can the corresponding alkoxide be formed?

A

Reaction of an alcohol with an alkali metal or with a strong base such as NaH

44
Q

What if the alkyl halide in the Williamson ether synthesis reaction was a secondary or tertiary alkyl halide?

A

The alkoxide will act as a base an an elimination reaction will take place

45
Q

What are the qualitative tests for alcohols

A

Jones test

Lucas test

Iodoform test

O Chem 2 (22 decks)

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