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Organic Chem II > Alcohol > Flashcards

Alcohol Flashcards

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1
Q

What only type of alcohol react rapidly with halogen under normal condition (25 celcius)? What mechanism?

A

low weight, water soluble tertiary alcohol

SN1

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2
Q

What type of alcohol reacts smoothly with halogen to form haloalkene? Under what conditions and mechanism?

A

1º alcohol

heat reflux with water

SN2

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3
Q

Boiling point of alcohol in order (1º, 2º, 3º)

Why?

A

1º > 2º > 3º

the less hinder steric structure, the easier to have intermolecular H-bonding -> the higher boiling point

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4
Q

Solubility of alcohol (1 OH group, 2 OH group, 3 OH group) in water in order?

A

The more OH group, the more soluble in water

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5
Q

The ease of rxn of alcohol w/ halogen? (1º, 2º, 3º)

A

1º < 2º < 3º

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6
Q

What type of alcohol are not useful to make haloalkene? Why?

A

1º with ß branching and 2º

because they produce racemic products

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7
Q

What type of alcohol reacts with PBr3? Mechanism? Conditions?

A

1º 2º

SN2

at Oº C

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8
Q

Under what conditions does the water insoluble tertiary alcohol reacts with halogen? What mechanism?

A

at O° C and in either ether or THF solvents

SN1

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9
Q

What solvents are used in rxn btw alcohol & SOCl2?

A

pyridine/ 3º amine

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10
Q

What type of alcohol reacts with SOCl2? Mechanism?

A

1º and 2º

SN2

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11
Q

Ease of acid catalyzed dehydration of alcohol in order (1º, 2º, 3º)?

A

1º < 2º < 3º

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12
Q

What compound is this? What is it character? What product it can help alcohol to make?

A

weak base, stable anion & good leaving group

haloalkene

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13
Q

What mechanisms for 2º & 3º alcohol react with halogen?

A

SN1

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14
Q

What type of alcohol react with H2CrO4 to give ketone?

What solvent?

A

2º alcohol

acetone

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15
Q

What type of alcohol react with PCC to give ketone?

What solvent?

A

2º alcohol

CH2Cl2

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16
Q

Why doesn’t 1º alcohol rxn with PCC result in carboxylic acid?

A

because PCC is used in solvent CH2Cl2 and not water

17
Q

What mechanism does 2º, 3º alcohol undergo for acid catalyzed dehydration rxn? What is the major product?

A

E1 mechanism

the most substituent alkene (best stabilized carbocation intermediate)

18
Q

What is the point of acid catalyzed dehydration of glycols? Mechanism?

A

to form ketone with the most stable carbocation intermediate

E1

18
Q

What are the products of oxidation of 1º alcohol by H2CrO4?

A

aldehyde & carboxylic acid

19
Q

What product does rxn of 2º alcohol with H2CrO4 give to?

A

ketone

20
Q

What product does rxn of 3º alcohol with H2CrO4 give to?

A

none = no rxn

21
Q

What compound is this? What type of alcohol does this compound reacts with? Mechanism? Conditions?

A

TsCl

1º, 2º
SN2

pyridine

22
Q

What mechanism does 1º ß-branching undergo for acid catalyzed dehydration alcohol? For normal 1º alcohol?

A

E1

E1, E2

23
Q

What type of alcohol and reagents react together to form aldehyde and final product carboxylic acid?

A

1º alcohol & H2CrO4 with acetone and water

24
Q

What type of alcohol react with PCC to give aldehyde?

What solvent?

A

1º alcohol

CH2Cl2

25
Q

glycol

A

compound with two hydroxyl (-OH) group

26
Q

Lewis structure of HIO4

A
27
Q

Lewis structure of H2CrO4

A
28
Q

Lewis structure of PCC ion

A
29
Q

What rxn to produce thiol from halogen?

A

R-X + Na+SH- -> Na-X + R-SH

30
Q

What products does the oxidation of R-SH give to?

A

sulfinic acid

disulfide

31
Q

Thiol Group

For H-bonding, is this group good or bad?

A
  • SH

bad

32
Q

What is the product of sulfinic acid oxidation?

A

sulfonic acid

33
Q

Lewis structure of sulfinic acid

A
34
Q

What is the point of oxidation of alcohol with HIO4?

A

to cleave glycol into two carbonyl group

35
Q

Tell solvents of each rxn with alcohol?

SOCl2

H2CrO4

PCC

TsCl

A

pyridine/ 3º amine

acetone

CH2Cl2

pyrdine & acetone

36
Q

What is the solvent for R-X + NaSH rxn? Mechanism

A

ethanol

SN2

37
Q
A

Organic Chem II (2 decks)

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