Exam 2 - Oxidation/Reduction

Question 1

Three important functional groups in oxidation:

Answer 1

aldehyde, ketone, carboxylic acid

Question 2

When reacting aldehydes/ketones with Grignards/Organolithiums, the ___ ___ attached to the Metal simply adds on the central C, eliminating the C=O double bond. H3O+ then converts the O- to ___.

Answer 2

R group (alkyl group), OH

Question 3

Oxidation = ___ hydrogens, not Cs.

Answer 3

removing

Question 4

A ___ alcohol can be oxidized to a ketone.

Answer 4

secondary alcohol

Question 5

Examples of Weaker Nucleophiles:

Answer 5

H2O, ROH

Question 6

An aldehyde reacting with a Grignard/Organolithium reagent and a follow-up H3O+ step, will produce a ___ ___.

Answer 6

secondary alcohol

Question 7

Oxidation - The substitution of ___ bonds for ___ bonds.

Answer 7

C-H bonds for C-X bonds

Question 8

Simplest aldehyde: ___

Answer 8

formaldehyde

Question 9

___ - The substitution of C-H bonds for C-X bonds (X = O,F,Cl,Br,I,N, etc.)

Answer 9

Oxidation

Question 10

___ ___ -> Acid-catalyzed and reversible.

Answer 10

Weaker Nucleophiles

Question 11

*Reminder: Grignard and Organolithium reagents CANNOT work around ___ ___ (i.e. ___). They need a separate ___ ___ step.

Answer 11

acidic protons (i.e. OH), separate acidic workup step (H3O+)

Question 12

In Pinnick Oxidation, an aldehyde reacts with the oxidants: NaClO2, NaH2PO4 to become a ___ ___.

Answer 12

carboxylic acid

Question 13

A secondary alcohol can become a ketone via the oxidants:

Answer 13

DMP, PCC, Swern oxidation (DMSO, NET3), and Jones Reagent (CrO3, H2SO4)

Question 14

You can cleave a ___ ___ with NaIO4!

Answer 14

vicinal diol

Question 15

A ketone reacting with a Grignard/Organolithium reagent and a follow-up H3O+ step, will produce a ___ ___.

Answer 15

tertiary alcohol

Question 16

Simplest organic molecule: ___

Answer 16

CH4 (methane)

Question 17

A ___ alcohol reacting with Jones Reagent (CrO3, H2SO4) will become a carboxylic acid.

Answer 17

primary alcohol

Question 18

A primary alcohol reacting with ___ ___ will become a carboxylic acid.

Answer 18

Jones Reagent (CrO3, H2SO4)

Question 19

A secondary alcohol can be oxidized to a ___.

Answer 19

ketone

Question 20

You can cleave a vicinal diol with ___!

Answer 20

NaIO4

Question 21

Examples of STRONG Nucleophiles:

Answer 21

RMgBr, RLi, OH-, CN-, LiAlH4, NaBH4

Question 22

A primary alcohol can become an aldehyde via the oxidants:

Answer 22

DMP, PCC, or Swern oxidation (DMSO, NEt3)

Question 23

Hydride-Reducing Agents such as ___ or ___ can convert aldehydes to primary alcohols, or ketones to secondary alcohols.

Answer 23

NaBH4, LiAlH4

Question 24

In ___ ___, an aldehyde reacts with NaClO2 and NaH2PHO4 to become a carboxylic acid.

Answer 24

Pinnick Oxidation

Question 25

Hydride-Reducing Agents such as NaBH4 or LiAlH4 can convert aldehydes to ___ \_\_\_, or ketones to ___ \_\_\_.

Answer 25

primary alcohols, secondary alcohols

Question 26

\_\_\_ = Removing hydrogens, not Cs.

Answer 26

Oxidation

Question 27

When using Hydride-Reducing Agents, remember that they need a separate ___ \_\_\_ step.

Answer 27

separate acidic workup step (H3O+)

Question 28

Strong Nucleophiles -\> ___ or \_\_\_.

Answer 28

Basic or Neutral

Question 29

Weaker Nucleophiles -\> ___ and \_\_\_.

Answer 29

Acid-catalyzed and reversible

Question 30

A primary alcohol can be oxidized to a(n) \_\_\_.

Answer 30

aldehyde

Question 31

Oxidation = Removing \_\_\_, not Cs.

Answer 31

hydrogens

Question 32

Hydride-Reducing Agents such as NaBH4 or LiAlH4 can convert ___ to primary alcohols, or ___ to secondary alcohols.

Answer 32

aldehydes, ketones

Question 33

In Pinnick Oxidation, an aldehyde reacts with the oxidants: ___ and ___ to become carboxylic acid.

Answer 33

NaClO2, NaH2PO4

Question 34

Tertiary carbons are usually ___ to oxidatoin.

Answer 34

unreactive

Question 35

\_\_\_ carbons are usually unreactive to oxidation.

Answer 35

tertiary

Question 36

A formaldehyde reacting with a Grignard/Organolithium reagent and a follow-up H3O+ step, will produce a ___ \_\_\_.

Answer 36

primary alcohol

Question 37

Aldehydes and ketones can also be reduced by catalytic reduction with ___ and \_\_\_. The problem here though, is that other functional groups such as ___ can get reduced first.

Answer 37

H2 and Pt/Ni, alkenes

Question 38

A ___ alcohol can be oxidized to an aldehyde.

Answer 38

primary alcohol

Question 39

In Pinnick Oxidation, a(n) ___ reacts with the oxidants: NaClO2 and NaH2PO4 to become a carboxylic acid.

Answer 39

aldehyde

Question 40

A primary alcohol reacting with Jones Reagent (CrO3, H2SO4) will become a ___ \_\_\_.

Answer 40

carboxylic acid

Question 41

You can ___ a vicinal diol with NaIO4!

Answer 41

cleave

Question 42

\_\_\_ ___ -\> Basic or Neutral.

Answer 42

Strong Nucleophile