Organic Chemistry: Chapter 12

Front 1

What does Oxidation result in?

Back 1

Oxidation results in an INCREASE in the number of C--Z bonds OR a DECREASE in the number of C--H bonds.

Front 2

What does Reduction result in?

Back 2

Reduction results in a DECREASE in the number of C--Z bonds OR an INCREASE in the number of C--H bonds!

Front 3

What is Z?

Back 3

Z can be O, N, S or P, typically.

Front 4

Metal hydride reagents act as a source of what? Why?

Back 4

Act as a source of H- because they contain polar metal-hydrogen bonds that place a partial negative charge on hydrogen.

Front 5

Reduction of an alkene forms what by the addition of what?

Back 5

Forms an alkane by addition of H2!

Front 6

Adding two equivalents of H2 to an alkyne forms what?

Back 6

An alkane!

Front 7

Adding one equivalent of H2 to an alkyne in a syn fashion forms what?

Back 7

Forms a cis alkene!

Front 8

Adding one equivalent of H2 to an alkyne in an anti fashion forms what?

Back 8

Forms a trans alkene!

Front 9

With the Lindlar catalyst, one equivalent of H2 added to an alkyne does what?

Back 9

Forms the cis alkene product which is unreactive to further reduction.

Front 10

What are two pathways to a hydride?

Back 10

NaBH4 and LiAlH4

Front 11

What do you react an alkyne with to get a trans alkene?

Back 11

Na and NH3!

Front 12

Are unhindered CH3X and primary alkyl halides more or less easily reduced than more substituted secondary and tertiary halides?

Back 12

MORE easily reduced.

Front 13

In unsymmetrical epoxides, where does the nucleophilic attack of H- occur?

Back 13

At the less substituted carbon atom!

Front 14

What oxidizing agents can form an epoxide?

Back 14

Peroxyacids with the structure RCO3H, mCPBA, PCC, OsO4, KMNO4, etc.

Front 15

When an alkene is reacted with an RCO3H, what happens to the stereochemistry?

Back 15

Trans stays trans and cis stays cis. Stereochemistry is retained!

Front 16

What is dihydroxylation?

Back 16

Dihydroxylation is the addition of two hydroxy groups to a double bond forming a 1,2-diol.

Front 17

What is anti-dihydroxylation? How many steps?

Back 17

Anti-dihydroxylation does the same thing as dihydrooxylation but in trans. It takes two steps to form: an epoxide then the trans product.

Front 18

What is syn-dihydroxylation?

Back 18

Syn-dihydroxylation forms two alcohols on the same side of the double bond.

Front 19

What is reacted with an alkene to form syn dihydroxylation?

Back 19

KMnO4 or OsO4

Front 20

What is reacted with an alkene to form anti dihydroxylation?

Back 20

RCO3H in water

Front 21

What is Oxidative Cleavage of an alkene?

Back 21

Oxidative cleavage is the breakage of both the sigma and pi bonds of the double bond to form two carbonyl groups.

Front 22

Cleavage with ozone is called what?

Back 22

Ozonolysis?

Front 23

Primary alcohols are oxidized to what two things?

Back 23

Aldehydes or carboxylic acids.

Front 24

Secondary alcohols are oxidized to what?

Back 24

Ketones!

Front 25

Tertiary alcohols are oxidized to what?

Back 25

Hahahaha! Again with the trick question! NO REACTION.

Front 26

What are 3 strong, nonselective oxidants used?

Back 26

CrO3, Na2Cr2O7, and K2Cr2O7

Front 27

What is a more selective, milder oxidant?

Back 27

PCC

Front 28

Primary alcohols are oxidized into aldehydes using what?

Back 28

PCC in CH2Cl2!

Front 29

Primary alcohols are oxidized into carboxylic acids using what?

Back 29

Any of the chromates, in the presence of a strong acid like H2SO4 and water!