Ch.11

Question 1

What is oxidation?

Answer 1

Addition of O or O2, loss of H2, Addition of X2

Question 2

What is reduction?

Answer 2

Addition of H2 or H-, Loss of O or O2, loss of X2

Question 3

What alcohols don’t get oxidized with chromic acid? When does oxidation take place?

Answer 3

Tertiary alcohols don’t get oxidized
Oxidation will only take place when carbon-carbon bonds are broken

Question 4

Pyridinium Chlorochroate (PCC)

Answer 4

Poisioned, slow reaction

Question 5

2º alcohol to a ketone, chromium and chromium-free

Answer 5

Chromium: chromic acid or PCC
Chromium-free: NaOCl, Swern, DMP

Question 6

1º alcohol to aldehyde

Answer 6

Chromium: PCC
Chromium-free: Swern, DMP

Question 7

1º alcohol to carboxylic acid

Answer 7

Chromium: chromic acid
Chromium-free: NaOCl

Question 8

When does an alcohol react as a nucleophile?

Answer 8

When the O-H bond breaks

Question 9

When does an alcohol react as an electrophile?

Answer 9

When the C O bond breaks

Question 10

Tosylate Ester

Answer 10

An ester of an alcohol with p-toluenesulfonic acid; great leaving group, can undergo both substitution and elimination

Question 11

What Nucleophiles work with the addition fo Ts

Answer 11

-OH, -CN, Br-, R’O-, NH3, LiAlH4

Question 12

How can you achieve the reduction of alchols

Answer 12

With two steps and Ts

Question 13

With HBR/H20 which alchols go by SN2 and which go by SN1

Answer 13

SN2: primary
SN1: secondary and tertiary

Question 14

What is the lucas reagent

Answer 14

HCl/ZnCl2

Question 15

How does the Lucas Reagent react with primary, secondary, and tertiary reagents

Answer 15

SN1 with tertiary and secondary
SN2 with primary

Question 16

What is the lucas test

Answer 16

a test used to determine whether an alcohol is primary, secondary, or tertiary.
<1 min tertiary
1-5 min secondary
>6 min primary

Question 17

When do phosphorus halides have good yields

Answer 17

With primary and secondary alcohols

Question 18

What phosphorus haldies react with chloride (primary, secondary, tertiary)

Answer 18

Primary: SOCl2
Secondary SOCl2
Tertiary: HCl

Question 19

What phosphorus haldies react with bromide (primary, secondary, tertiary)

Answer 19

Primary: PBr3 or HBR
Secondary: PBr3
Tertiary: HBr

Question 20

What phosphorus haldies react with Iodide (primary, secondary, tertiary)

Answer 20

Primary: P/I2
Secondary P/I2
Tertiary: HI

Question 21

What does thionyl chloride do

Answer 21

Converts alcohols into the corresponding alkyl chlorides

Question 22

In alcohol dehydration, what does H2SO4 produce

Answer 22

alkenes

Question 23

What temperature and mechanism does the dehydration of alcohols occur?

Answer 23

High temperature (180 and above)
E1 Mechanism

Question 24

What is the rate-limiting step in the dehydration reactions of alcohols

Answer 24

the formation of the carbocation

Question 25

Bimolecular Dehydration

Answer 25

Two alcohols react by SN2 to form an ether
Favored by low temperatures (140ºC and below)

Question 26

Pinacol Rearrangement

Answer 26

A vicinal diol converts to a ketone under acidic conditions and heat

Question 27

Fischer Esterification

Answer 27

the acid-catalysed reaction of an alcohol with a carboxylic acid to form an ester; equilibrium driven

Question 28

Williamson Ether Synthesis; best results, mechanism

Answer 28

Primary (best result): SN2
secondary of tertiary: E2