Chapter 7-9 Reagents

Question 1

Strong Base / Weak Nucleophile

Answer 1

DBN, DBU, NaH

Question 2

Strong Base / Strong Nucleophile

Answer 2

NaOH, NaMeO, NaEtO, (T-buok)

Question 3

Weak Base / Strong Nucleophile

Answer 3

I, Br, Cl, Hs, Rs, RSH, H2S

Question 4

Weak Base / Weak Nucleophile

Answer 4

H2O, EtOH, MeOH

Question 5

HBr—>

double bond.

Answer 5

Adds Br on the most substituted carbon.

Addition.

Question 6

Br2–>

double bond.

Answer 6

Adds a 2 Br molecules. One will be wedge one will be dashed.

Adds across the double bond

Question 7

Br2,H2O

double bond.

Answer 7

Br molecule added on the least substituted carbon.
OH added on the most substituted carbon.
Will produce an En

Double bond.

Question 8

BH3•THF
—————->
H2O2NaOH

Answer 8

Adds a OH molecule on the least substituted carbon.

Produces an En.

Watch for creation of chiral centers.

Question 9

H3O+

Double bond

Answer 9

Adds a OH molecule on the most substituted carbon.

Question 10

KMNO4
——————>
NaOH + Cold

Double bond.

Answer 10

Two OH molecules added SYN across double bond.

Will produce an En

Question 11

OSO4
——————>
NaHsO3,H20

Double bond

Answer 11

Two OH moles added SYN across the double bond.

Question 12

O3
———>
DMSO

Double bond

Answer 12

Break at double bonds.

Question 13

Pt
———->
H2

Double bond

Answer 13

Removes double bonds.

Question 14

Hg(OAc)2,H2O
———————>
NaBH4

Double bond

Answer 14

Adds OH molecule on the most substituted carbon

Question 15

RCO3H
———->
H3O+

Answer 15

Two OH molecules added across the double bond. In Anti formation. One dash. The other Wedge
Produces an En

Question 16

xs Br
——->

Terminal Triple bond.

Answer 16

Alkyne to Alkane. Adds two molecules of Br to the most substituted carbon.

Question 17

1.) xs NaNH2
—————>
2.) H2O

Terminal triple bond.

Answer 17

Eliminates Molecules bonded to carbons.

Turns alkanes to Alkynes.

Question 18

H2
——->
Lindlars Cat

R- triple -R

Answer 18

Turns an alkyne to a Alkene with a CIS conformation.

Question 19

H2
——>
Pt

R-triple-R

Answer 19

Removes all triple bonds.

Turns it into Trans conformation.

Question 20

1.) O3
——>
2.) H2O

Terminal triple bond.

Answer 20

Adds double bonded O to the most substituted carbon. Also adds a carbon with two double bonded O’s

Question 21

xs Cl2 [one Eq]
———->
CCl4

Terminal triple bond.

Answer 21

Turns a Alkyne to a Alkene adds a Cl to the least and most substituted carbons

Question 22

xs Cl2 [Two Eq]
———->
CCl4

Terminal triple bond

Answer 22

Turns a Alkyne to a Alkane and adds two CL molecules on the most substituted carbon and the least substituted carbon.

Question 23

1.) R2BH
———->
2.) H2O2NaOH

Terminal triple bond

Answer 23

Add an Double bonded O to the least substituted carbon and the add a H bond off of that.

ALDEHYDE.

Question 24

HgSO4
————>
H2SO4, H2O

Terminal triple bond.

Answer 24

Add a double bonded O to the most substituted carbon.

KETONE

Question 25

1.) NaNH2
————>
2.) MeI or EtI or a bond structure.

Terminal triple bond.

Answer 25

Use this to add carbon bonds on a Alkyne.

Question 26

Na
——>
NH3 (l)

R-triple-R

Answer 26

Turns an Alkyne to an Alkene with a Trans connectivity