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PMP-102 > Alcohols, Ethers, and Epoxides > Flashcards

Alcohols, Ethers, and Epoxides Flashcards

1
Q

-OH groups are polar or nonpolar?

A

polar

soluble in water - important in drugs

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2
Q

primary alcohol (carbinol carbon atom):

A

C-OH wich 2H bonded to C
1Rgroup

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3
Q

secondary alcohol (carbinol carbon atom):

A

C-OH
1H bonded to Cand 2R groups

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4
Q

teritary alcohol (carbinol carbon atom):

A

C-OH with 3R groups attached to the C

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5
Q

Alcohols can form hydrogen bonds. Two further important properties:

A
  1. Alcohols are soluble in water
  2. Molecules with alcohol groups can H-bond to proteins
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6
Q

what are the 2 steps of Synthesis of Alcohols?

A
  1. Nucleophilic substitution on an alkyl halide
  2. Synthesis of alcohols from alkenes
  3. Addition of acetylides to carbonyl compounds (C=O)
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7
Q
  1. Synthesis of alcohols from alkenes
    3 parts and product
A

a. Acid-catalysed hydration

b. Oxymercuration–demercuration

c. Hydroboration–oxidation

Markovnikov product&raquo_space;> Anti-Markovnikov product

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8
Q

What reagent does Markovnikov need for dehydration reaction?

A

Boron

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9
Q

What reagant does Anti-Markovnikov need for dehydration reaction?

A

Mercury

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10
Q

Organometallic compounds

A

covalent bonds between carbon atoms and metal atoms

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11
Q

Nucleophilic carbon atoms > organometallic
> gets attacked by

A

a strong nucleophile

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12
Q

Most alkyl and alkenyl groups are not ______ enough to be deprotonated by NaNH2

A

acidic

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13
Q

Grignard and organolithium reagents:

A

strong nucleophiles/strong bases

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14
Q

Nucleophilic reactions are additions of what group?

A

carbonyl (C=O) groups

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15
Q

Organometallic reagents for alcohol synthesis 3 steps

A

1) Formation of the Grignard reagent

2) The Grignard reagent attacks a carbonyl compound to form an alkoxide salt

3) After the first reaction is complete, water/dilute acid is added to protonate the alkoxide and give the alcohol

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16
Q

[primary] formaldehyde when reagent attacks the C

A

the lone pair of e will shift to the O and form a primary alcohol

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17
Q

secondary aldehyde froms what type of alcohol

A

secondary

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18
Q

ketone forms what type of alcohol

A

tertiary (3)

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19
Q

Reduction of the C=O: synthesis of 1° and 2° alcohols

A

Reduction of the C=O: synthesis of 1° and 2° alcohols

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20
Q

Sodium borohydride (NaBH4)
are involved in what two processes

A

1) Borohydride transfers a hydride ion (H:-) to carbon, forming an alkoxide ion

2) The alcohol solvent protonates the alkoxide

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21
Q

What is being reduced in the second step of synthesis of 1st and 2nd alcohols and what does NOT reduce?

A

Reduces ketones (2˚alcohols)

Reduces aldehydes (1˚ alcohols)

Does not reduce carbonyl groups: acids, esters, and other acid derivatives

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22
Q

LiAlH4 v NaBH4

A

LiAlH4 much stronger reagent

Easily reduces ketones (2˚alcohols) and aldehydes (1˚ alcohols)

Reduces carbonyl groups (1˚ alcohols): acids, esters, and other acid derivatives

23
Q

Hydride reagents add a hydride ion (H:-), reducing the C=O to an alkoxide ion

what reagent is used?

A

Lithium aluminium hydride (LiAlH4)

24
Q

2 steps to reduction of Reduction of the C=O: synthesis of 1° and 2° alcohols using LiAlH4:

A
  1. LAH transfers a hydride ion (H:-) to carbon, forming an alkoxide ion
  2. After the first reaction is complete, water/dilute acid is added to protonate the alkoxide
25
Q

Inorganic chemistry

A

oxidation/reduction is a loss/gain of electrons i.e. Cr6+to Cr3+

26
Q

oxidation is

A

adding an oxidising agent (O, O2, Br2, etc.) or losing H2

27
Q

reduction is

A

is adding a reducing agent (H2, NaBH4, H-etc.) or losing O, O2 or X2

28
Q

neither an oxidation nor a reduction: addition or loss of…

A

H+, -OH, H2O, HX, etc.

29
Q

oxidation usually converts C-H bonds to

A

C-O bonds

30
Q

name the 3 steps of Oxidation of alcohols:

A
  1. Oxidation of primary alcohols to carboxylic acids
  2. Oxidation of primary alcohols to aldehydes
  3. Oxidation of secondary alcohols to ketones
31
Q

Why is it important for our bodies to detoxify alcohol?

A

keep it from building up in blood and poisoning the brain

32
Q

ethanol - 1 alcohol is transformed to

A

acetaldehyde

33
Q

methanol > formaldehyde >

A

formic acid

34
Q

a weak nucleophile (alcohol) will attack the strong electrophile. what will happen to the charge on the oxygen?

A

the +ive charge will move from the C to the O

O will start with 2 lone pairs and then end up with only one because one is taken up by H and the other by the C that had been attacked by the nucleophile

35
Q

what do we add to a weak nucleophile to make a strong nucleophile?

A

Na

this will break the bond between the O-H, H will leave the O and leave O with 3 lone pairs with a -ive charge

36
Q

alcohols - strong nucleophile = lone pair from O will attack the C in the ____ ________

A

weak electrophile which will attach the the alcohol (weak nucleophile)

37
Q

how to turn poor electrophile to a good electrophile?

A

add HBr as the extra H will attach to the oxygen taking up the lone pair and leaving a +ive charge

Br- will be by itself

BETTER LEAVING GROUP (ACTIVATE THE OH)

38
Q

Convert –OH to a better tosylate leaving group
step 1 and 2

A

Step 1: Activation to tosylate
Step 2: SN2 displacement of tosylate ion (-OTs)

In 2 steps, an alcohol is transformed to a different functional group through a
SN2 reaction

39
Q

in an SN reaction should R group be hindered or unhindered?

A

R must be an unhindered primary or secondary alkyl group if substitution is to predominate over elimination

40
Q

n

A
41
Q

in the conversion of alcohols to alkyl halides what reaction is teritary and secondary?

what about primary?

A

SN1
SN2

42
Q

how to form ethers?

A

bimolecular condensation

reaction that joins two (or more) molecules, often with the loss of a small molecule such as water

43
Q

acidic dehydration conditions two reactions compete:

A

A) Elimination, dehydration to give an alkene
B) Substitution, condensation to give an ether

44
Q

What do we call forming an ester in alcohols?

A

Esterification of alcohols

45
Q

explain esterification of alcohols

A

Replacing the -OH group of a carboxylic acid with the -OR group of an alcohol

46
Q

Inorganic esters

A

the alkoxy ( -OR) group replaces a –OH of an inorganic acid

47
Q

The Williamson ether synthesis

A

Alkoxide ion reacts with primary alkyl halides and tosylates to form ethe

48
Q

ether synthesis = if alkyl halide is hindered?
what process will happen

A

elimination

49
Q

what are ethers?

A

O-R’.
R may be alkyl group or aryl group

[aryl - functional group derived from an aromatic]

50
Q

Most common methods for ethers preparation:
Williamson synthesis and bimolecular condensation of alcohols

A
  1. Peroxyacid epoxidation
51
Q

Opening of epoxide: 1. Acid-Catalysed

A

a. In water to form glycols
b. In alcohols to form an alkoxy alcohol
c. Using hydrohalic acids

52
Q

b. In alcohols to form an alkoxy alcohol

Protonation of oxygen (forming a good leaving group), followed by the alcohol attack as if it were an ….

A

SN1-type reaction The alkoxy group bonds to the more highly substituted carbon

53
Q

a. In water to form glycols

Protonation of oxygen (forming a good leaving group), followed by….

A

SN2 attack by water

54
Q

second part of opening of epoxide

  1. Base-catalysed
A

a. with alkoxides or hydroxide [The alkoxide ion simply attacks the less hindered carbon atom in an SN2 displacement]

b. with organmetallics [Carbanion usually attacking the less hindered epoxide carbon atom:
R bonds to the less substituted carbon]

PMP-102 (49 decks)

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