Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

O Chem 2 > Alcohols > Flashcards

Alcohols Flashcards

You may prefer our related Brainscape-certified flashcards:
AP® Chemistry flashcards Periodic Table flashcards Chemistry 101 flashcards Organic Chemistry 101 flashcards
1
Q

List 2 methods to synthesize alcohols

A

Using Grignard reagents

Reduction of carbonyl compounds

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

What are aldehydes reduced to?

A

Primary alcohols

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

What are ketones reduced to?

A

Secondary alcohols

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

What primary alcohols are soluble in water?

A

Small alcohols, five carbons or fewer.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

Why are small alcohols soluble in water?

A

Small alcohols participate in hydrogen bonding with water molecules

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

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

A

Oxonium ion

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

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

A

Alkoxide ion

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

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

A

Acidity decreases, pka increases, ka decreases

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

Why do substituents reduce alcohol acidity?

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

Use biological oxidation to explain what becomes of ethanol

A

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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

What does ethylene glycol oxidize to?

A

To oxalic acid, which is toxic

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
17
Q

Using acyl chlorides, name the reagents and products of esterification

A

Reagents: alcohol + acid chloride

Product: ester + HCl

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
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)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions