Chapter 10 Reactions

Question 1

Alkoxide Synthesis
(Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity)

Answer 1

Reactants: Alcohol, 2Metal (Na,Li,K), MH
Catalysts/Conditions: none

Products: Williamson Ether (O-Na+)
Intermediate: None
Regioselectivity: None
Stereoselectivity:None

Question 2

Alcohol-Haloalkene Conversion

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 2

Reactants: Alcohol, HX
Catalysts/Conditions: H2O

Products: Haloalkane
Intermediate: 1* = Sn2, 3= Sn1, 2 = both (mostly Sn2)
Regioselectivity: Depends
Stereoselectivity: Depends

Question 3

Alcohol-Haloalkane Conversion (Phosphorus Tribromide)

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 3

Reactants: Alcohol, PBr3
Catalysts/Conditions: none

Products: Bromoalkane, H3PO3
Intermediate: Sn2 reaction, no intermediate
Regioselectivity: 1* and 2* alcohols, no 3*
Stereoselectivity: inversion of configuration

Question 4

Alcohol-Haloalkane Conversion (Thionyl Chloride)

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 4

Reactants: Alcohol, SOCl2
Catalysts/Conditions: pyridine

Products: Chloroalkane
Intermediate: Sn2, no intermediate
Regioselectivity: 1* and 2* alcohols, no 3*
Stereoselectivity: inversion of configuration

Question 5

Alcohol-Aryl Sulfonate Conversion

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 5

Reactants: Alcohol, TsCl
Catalysts/Conditions: pyridine

Products: R-OTS
Intermediate: None
Regioselectivity: None
Stereoselectivity: Stereochem doesn’t change

Question 6

Dehydration of Alcohols

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 6

Reactants: 1. Alcohol, H2SO4 2. H2O
Catalysts/Conditions: heat

Products: Alkene
Intermediate: E1 (carbonation intermediate)
Regioselectivity: 3>2, no 1* or methyl
Stereoselectivity: Zaitsev major, Hoffman minor

Question 7

Alcohol Oxidation (Presence of H2O)
(Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity)

Answer 7

Reactants: Alcohol, H2CrO4 (Or Jones Reagent)
Catalysts/Conditions:

Products: Carboxylic acid
Intermediate: none
Regioselectivity: 1* or 2*
Stereoselectivity: None

Question 8

Pinacol Rearrangement
(Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity)

Answer 8

Reactants: Glycol (a 1,2 diol), H2SO4
Catalysts/Conditions: heat

Products: Ketone
Intermediate: Alkyl shift so that C+ is on C w/ OH group
Regioselectivity: None
Stereoselectivity: None

Question 9

Periodic Acid Oxidation of Glycols

Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity

Answer 9

Reactants: Glycol, HIO4
Catalysts/Conditions: none

Products: Aldehydes/Ketones (Splits molecule)
Intermediate: None
Regioselectivity: None
Stereoselectivity: In cyclic glycols, only cis glycols work

Question 10

Alcohol Oxidation (Absence of H2O)
(Reactants (including conditions/catalysts), Products, Intermediates, Regioselectivity, Stereoselectivity)

Answer 10

Reactants: Alcohol, PCC
Catalysts/Conditions: DCM

Products: 1* and 2* alcohols into aldehydes
Intermediate: none
Regioselectivity: none
Stereoselectivity: none

Question 11

Primary alcohols can be oxidized to:

Answer 11

Aldehydes, which can then be oxidized to carboxylic acids.

Question 12

Secondary alcohols can be oxidized to:

Answer 12

ketones.

Question 13

Tertiary alcohols can be oxidized to:

Answer 13

nothing. They don’t oxidize.