Exam 2 review

Question 1

What could you use to reduce a ketone but not a carboxylic acid?

Answer 1

To a secondary alcohol:
NaBH4 /CH3OH
H2/cat.

To an Alkane:
Zn(Hg), HCl
N2H4/ KOH heat

Question 2

What will reduce a carboxylic acid to a primary alcohol?

Answer 2

LiAlH4, ether/ H3O+

Question 3

How do you form a methyl ester?

Answer 3

Carboxylic acid reacting with diazomethane (CH2=N=N) in ether solvent.

Question 4

What oxidizes a primary ROH to and aldehyde?

Answer 4

PCC/CH2Cl2

Question 5

What oxidizes a secondary ROH to a ketone?

Answer 5

PCC/CH2Cl2

Question 6

What can oxidize an aldehyde or a primary ROH to a carboxylic acid?

Answer 6

H2CrO4

Question 7

What reduces a ONLY ketones and aldehydes down to an alcohol?

Answer 7

NaBH4/EtOH

Question 8

What reduces: 
Aldehydes
Ketones
Carboxylic acids 
Imines

Answer 8

LIAlH4/Et2O

Question 9

What reduces everything EXCEPT carboxylic acids?

Answer 9

H2/catalyst

Question 10

What is the difference between H2/pt and H2/Rh?

Answer 10

H2/Rh will not reduce a carbonyl

Question 11

If you react a grignard with CO2 and acid w/u you will produce…

Answer 11

A carboxylic acid

Question 12

COOH + primary ROH in TsOH

Is an example of what reaction?

Answer 12

Fischer esterification

Question 13

Examines act as a nucleophile and attack ______ and _______.

Answer 13

Acid chlorides and alkyl halides

Question 14

AcetoAcetic Ester is formed by a claisen with two parts of ethyl acetate. AAE will form a mono/disubstituted ________.

Answer 14

Acetone. (Where one R group is a methyl)

Question 15

Malonic ester produces mono/disubstituted _______.

Answer 15

Acetic acid. (Where one R group is an OH)

Question 16

What reaction produces a new C-C bond at the B-position?

Answer 16

Michael addition

Question 17

Always check for ______ once you’ve found the end product.

Answer 17

Chiral centers

Question 18

Hydrolysis of a _________ will form a carboxylic acid.

Answer 18

Carboxylic acid derivative

Question 19

Hydrolysis of carboxylic derivative in basic conditions forms the _______ .

Answer 19

Carboxylate

Question 20

In a self claisen, you need a ______ for the deprotonated a-carbon.

Answer 20

Acid work up step

Question 21

In order for Decarboxylation to occur, you need a _______.

Answer 21

B-carbonyl

Question 22

What are the 5 derivatives of a carboxylic acid?

Answer 22

Acid chlorides, anhydride, esters (lactones), amides (lactams), nitriles