Exam 2 - Nitrogen Nucleophile Reactions + Alkane Reduction Reactions

Question 1

*Imine formation is sensitive to the amount of ___.

Answer 1

acid

Question 2

You can react a ketone/aldehyde with a ___ ___, and catalytic ___ ___, in order to make an enamine.

Answer 2

secondary amine and catalytic acetic acid

Question 3

imine = ___ ___ ___.

Answer 3

C=N double bond

Question 4

The Clemenset Reaction is NOT good for ___ groups.

Answer 4

acid-sensitive

Question 5

In the Clemenset Reaction, you add Zn(Hg) and HCl to a ketone/aldehyde in order to completely reduce it to a(n) ___.

Answer 5

alkane

Question 6

The Wolf-Kishner Reaction will NOT work with ___ molecules.

Answer 6

base-sensitive molecules

Question 7

The Wolf-Kishner Reaction will ___ work with base-sensitive molecules.

Answer 7

NOT

Question 8

Hydrozine is ___.

Answer 8

H2N-NH2

Question 9

In the ___ ___, you add Zn(Hg) and HCl to a ketone/aldehyde in order to completely reduce it to an alkane.

Answer 9

Clemenset Reaction

Question 10

___ ___ is a good acid for imine formation.

Answer 10

Acetic acid

Question 11

*Remember, that reducing agents such as NaBH4 or LiAlH4 will simply react with the ___/___ first.

Answer 11

ketone/aldehyde

Question 12

A ketone/aldehyde can react with a ___ ___ and catalytic ___ ___, in order to produce an imine.

Answer 12

primary amine (R-NH2 or NH3) and catalytic acetic acid

Question 13

In the Wolf-Kishner Reaction, you add H2N-NH2 (hydrozine), KOH, and heat to a ketone/aldehyde in order to completely reduce it to a(n) ___. It also produces ___ byproduct.

Answer 13

alkane, N2 (gas)

Question 14

The ___ ___ is NOT good for acid-sensitive groups.

Answer 14

Clemenset Reaction

Question 15

In the Wolf-Kishner Reaction, you add ___, ___, and ___ to a ketone/aldehyde in order to completely reduce it to an alkane.

Answer 15

H2N-NH2 (hydrozine), KOH, and heat

Question 16

In the Clemenset Reaction, you add ___ and ___ to a ketone/aldehyde in order to completely reduce it to an alkane.

Answer 16

Zn(Hg) and HCl

Question 17

The Clemenset Reaction is ___ good for acid-sensitive groups.

Answer 17

NOT

Question 18

In reductive amination, a ketone or aldehyde reacts with a ___ ___ (i.e. ___), catalytic ___ ___, and a ___ ___, in order to produce an amine.

Answer 18

primary amine (R-NH2), catalytic acetic acid, reducing agent (NaCNBH3 or NaBH(OAc)3)

Question 19

___ is H2N-NH2.

Answer 19

Hydrozine

Question 20

*You ___ ___ want texas carbons when doing synthesis questions (reverse mechanisms) with imine/enamine formation. Only some key parts will work together!

Answer 20

DO NOT

Question 21

In imine formation, if a ketone reacts with a primary amine (R-NH2) and catalytic acetic acid, then the final product will effectively replace the ketone C=O with ___.

Answer 21

C=N-R

Question 22

*Note: ___ ___ acid will protonate the amine, BUT you need ___ acid in order to protonate the OH into a good LG (make H2O).

Answer 22

too much, some

Question 23

In enamine formation, if a ketone reacts with a secondary amine, catalytic acetic acid, and Na2SO4 dessicant, the final product will be the ___ ___, with the N-H bond replaced with ___.

Answer 23

secondary amine with (an alkene between the ketone’s R groups) added where the N-H was

Question 24

Nitrogen nucleophiles are ___! Need to know both forward and backward mechanisms.

Answer 24

reversible

Question 25

The ___ ___ will NOT work with base-sensitive molecules.

Answer 25

Wolf-Kishner Reaction

Question 26

In the ___ ___, you add H2N-NH2 (hydrozine), KOH, and heat to a ketone/aldehyde in order completely reduce it to an alkane.

Answer 26

Wolf-Kishner Reaction

Question 27

___ = C=N double bond.

Answer 27

imine

Question 28

*Note: You can use ___ acids in the reverse mechanism for imine formation.

Answer 28

strong acids