Chapter 16 Reagents

Question 1

NaBH4 in MeOH with Aldehyde or Ketone

Answer 1

=O turns into -OH and -H. Works with both Aldehydes and Ketones.

Question 2

C6H5MgBr

Answer 2

=O turns into -OH, -C6H5 is added alongside the carbon of the carboxyl group. Works with both Aldehydes and Ketones.

Question 3

LiAlH4, then H2O

Answer 3

=O turns into -OH and -H. Works with both Aldehydes and Ketones.

Question 4

Ag2O, HO- (with and without acid)

Answer 4

the terminal hydrogen of the aldehyde component turns into an O-. Works with only Aldehydes.

if with acid, turns into OH

Question 5

(C6H5)3P+ R-

Answer 5

Replaces =O with =R. Works with both Aldehydes and Ketones.

Question 6

H2 and Pt

Answer 6

=O turns into -OH and -H. Works with both Aldehydes and Ketones

Question 7

HO-R-OH and HA

Answer 7

Forms a ring where the double bond O was. (The =O turns into -O,-O that are connected with the R group) Works both Aldehydes or ketones

Question 8

Ag(NH3)2+

Answer 8

Replaces the H with O-, yields silver. Works only with Aldehydes.

Question 9

Hydroxylamine (HONH2)

Answer 9

Replace =O with =N-OH. Works with both Aldehydes and Ketones

Question 10

Phenylhydrazine (PH-NHNH2)

Answer 10

Replace =O with =NNHPh. Works with both Aldehydes and Ketones

Question 11

HNO3 +H2SO4

Answer 11

Replace a hydrogen with NO2, depending on the directing factor. For benzene rings.

Question 12

C6H5NHNH2

Answer 12

Replace =O with =NNHPh. Works with both Aldehydes and Ketones

Question 13

H2C:- +P(C6H5)3

Answer 13

Replace =O with =R (in this case CH2). Works with both Aldehydes and Ketones.

Question 14

1)C6H5MgBr 2)NH4Cl

Answer 14

Replace =O with -OH, -C6H5 is added alongside the carbon of the carboxyl group. Works with both Aldehydes and Ketones.

Question 15

H2NNH2, HO-, heat

Answer 15

Replace =O with hydrogens. Works with both Aldehydes and Ketones.

Question 16

PCC or Swern

Answer 16

-OH is replaced with =O, hydrogen is removed. Works with 1* and 2* alcohols to give aldehydes and ketones.

Question 17

Pyridine/CrO3

Answer 17

-OH is replaced with =O, hydrogen is removed. Works with 1* and 2* alcohols to give aldehydes and ketones.

This is another way to write PCC

Question 18

H2CrO4

Answer 18

-OH is replaced with =O, hydrogen is removed. Works with 2* alcohols to give ketones.

Question 19

KMnO4

Answer 19

-OH is replaced with =O, hydrogen is removed. Works with 2* alcohols to give ketones

Will also convert aldehydes to carboxylic acids (-H to -OH)

Question 20

NaCN

Answer 20

Replace =O with -OH and -CN. Occurs with both Aldehydes and Ketones.

Question 21

Primary Amine (NH2R) +HA

Answer 21

Replace =O with =NR. Occurs with both Aldehydes and Ketones.

Question 22

Secondary Amine (NHR2) +HA

Answer 22

Replace =O with -NR2 and a double bond on more substituted carbon. Occurs with both Aldehydes and Ketones.

Question 23

Zn/Hg/HCl

Answer 23

=O is replaced with 2 H’s. Occurs with both Aldehydes and Ketones.

Question 24

EtSH

Answer 24

Replace =O with two -SEt. Occurs with both Aldehydes and Ketones.

Question 25

SHRSH

Answer 25

Replace =O with two single bonds to a SRS. Occurs with both Aldehydes and Ketones.

Question 26

SOCl2

Answer 26

Replaces -OH with -Cl. Occurs with Alcohols that aren’t 3*

Question 27

NaBH4 with carboxylic acids, esters, and acyl chlorides

Answer 27

Reduce carboxylic acids, esters, and acyl chlorides to aldehydes

Replaces -Cl, -OR, and -OH with hydrogens

Question 28

LiAlH(OtBu)3 with Et2O in H2O

Answer 28

Reduce carboxylic acids, esters, and acyl chlorides to aldehydes

Replaces -Cl, -OR, and -OH with hydrogens

Same as NaBH4, but stronger so needs to be weakened