Alcohols And phenols Flashcards

(37 cards)

1
Q

Describe alcohol nomenclature

A

1) find longest parents with the OH substituents at the lowest number
2) OH takes highest priority so name the parent chain “alkan-#-ol”
3)if there is more than 1 it is named as “alkanediol or alkanetriol “ ect

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

Ether nomenclature (R-O-R)

A

1) no priority against anything
2) acts purely as a substitutent
3) drop “yl “ add oxy

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

What is a phenol?

A

A benzene ring with an OH group

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

Which is more acidic, OH or a phenol and why

A

Phenol has resonance

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

What is a grinyard?

A

R-MG-X group

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

What yields no reaction when reacted with a grinyard ?

A

R-X

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

Aldehyde

A

R-(c=O)-H

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

Ketone

A

R-(c=O)-R

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

Carboxcylic Acid

A

R-(c=O)-OH

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

When does Jones, and SWERN or PPC yield no reaction?

A

3 degree OH

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

Describe Jones reaction and reagents

A

The reagents are Cr2O7(-2) + Acid or CrO3 + acid

1 degree alcohol:

The two h’s on the parent carbon disappear and a double bond to an oxygen takes its place. Basically, we stop once a carboxylic acid is formed

2 degrees OH:

Stop at a ketone

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Describe PCC AND SWERN

A

these reagents are less reactive so always stop at aldehyde

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

How can we prepare a RO( - ) group from a ROH group? Hint: 2 methods

A

1) deprotenate with a strong base but NEVER NAOH unless it’s a phenol

2) deprotenate with elemental metal in the form 2k or 2Na

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

Describe the two ways to prepare ROH from an alkyl halide and list any restrictions or rearrangements

A

1) SN2 with OH as a nu

-great for any 1 degree Halides, including allylic and benzyllic positions
-NEVER ON 2 (produces alkene) or 3 (NR) degree halides

2) SN1 with water as the nu

-rearrangements are possible
-great for 3 degree or 2 degree halides

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

How do you prepare ROH from alkenes? 3 options

A

1) use Hydroboration Oxidation for antimarkovnikov

2) Use Oxymercuration demurcuration for MARK OR H3O+ (for rearrangement if necessary)

3) Use oxidation for the addition of 2 SYN alcohol groups

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Hydroboration reagents and type

A

1) BH3, THF
2) H2O2, NaOH

Anti mark

17
Q

Oxymercuration demurcuration reagents and type

A

1) Hg(OAC)2, H2O
2) NaBH4

Markovnikov

18
Q

Oxidation reagents

A

KMnO4

OR

OsO4

19
Q

How do we turn a ketone or aldehyde to an alcohol?

A

We use a Nu and an Acid Work up. Use a nu to open up the pi bond then react react the O with the strong acid to potentate it.

The nu can be

  • RC (triple bond) C(-)
  • RMgX
  • LiAlH4
20
Q

How do you prepare organometallics?

A

React a R-X group with elemental metal

21
Q

What preparation of organometallics results when we react a halide with elemental Mg?

A

The magnesium wedges itself in between the R group and the Br and the carbon acts as the Nu

22
Q

What happens when an R-X group reacts with elemental Li

A

The X group leaves and is replaced by lithium and the carbon now acts as a NU

23
Q

What happens when we react grignyards with H20 or OH? Even D2O

A

The grinyard leaves and is replaced with a H or a D depending on which reagent was used

24
Q

What happens when you react an organolithium with a 1) ketone in THF and 2) an acid work up?

A

The pi bond of the oxygen breaks open and has O- on one side and the R group of the organolithium on the other line. Then the acid work up pronates the O to form an oxygen

25
How do we get from a ketone to an alcohol and R group on the same carbon?
Organolithium and acid work up
26
What happens when an organometallics reacts with an alkyl halide?
NOTHING
27
How do we go from a ketone to an alcohol group
Use a hydride Nu, like LiAlH4, or NaBH4 along with an acid work up
28
Describe the process of hydride Nu
Attack the carbon double bounded to the oxygen in a ketone. Breaks the ketone up into a negative oxygen and an H. The acid work up protenates the O into an alcohol
29
What are two hydride Nu?
LiAlH4 and NaBH4
30
Describe how to get from an alcohol to a alkyl halide or Nu
Use TsCl and a Base . The OH group becomes OTs then is a good leaving group. This reacts with a X group or a Nu
31
Describe how to get from an OH to an H
1) TsCl, Base 2) NaH The H replaces the OH
32
Describe how to get from an OH to two adjacent H’s
Dehydrate to an alkene with water and a strong acid. Then use H2 and platinum to remove the double bond and add two Hs
33
How can we convert an OH group to a alkyl halide without using a tosalate
H-BR
34
What does SOCl2 and thionyl chloride do as reagents
Replaces OH with Cl
35
What does PBr3 and phosphorus tribromide do as reagents
Replace OH with Br
36
What does P, I2 do as a regents
Replaces OH group with I
37
What does 1) PBr3 and 2) Li metal Do as reagents ?
Replaces OH group with Li group