CHAPTER 19ENOLATE ANIONS AND ENAMINES

MULTIPLE CHOICE
1. How many different aldols (-hydroxyaldehydes), including constitutional isomers and stereoisomers,
are formed upon treatment of butanal with base?
a. 1
b. 2
c.
d. !

2. How many -hydroxy"etones, including constitutional isomers and stereoisomers, are formed upon
treatment of acetone with base?
a. 1
b. 2
c.
d. !

. How many different -hydroxyaldehydes and -hydroxy"etones, including constitutional isomers and
stereoisomers, are formed upon treatment of a mixture of acetone and ben#aldehyde with base?
a. 1
b. 2
c.
d. !

!. How many different -hydroxyaldehydes and -hydroxy"etones, including constitutional isomers and
stereoisomers, are formed upon treatment of a mixture of acetone and acetophenone with base?
a. !
b. $
c. %
d. 12

&. How many different -hydroxyaldehydes and -hydroxy"etones, including constitutional isomers and
stereoisomers, are formed upon treatment of a mixture of butanal and acetone with base?
a. !
b. $
c. %
d. 12

'rown Organic Chemistry $e (est 'an" 1
$. )hich of the following are intermediates in the acid cataly#ed aldol reaction of propanal to form 2-
methyl-2-pentenal?
1. enol
2. enolate
3. tetrahedral carbonyl intermediate
4. aldol
a. only 1 and 2
b. only 1, 3 and 4
c. only 2, 3 and 4
d. 1, 2, 3 and 4

*. )hich of the following are intermediates in the base cataly#ed aldol reaction of propanal to form 2-
methyl-2-pentenal?
1. enol
2. enolate
3. tetrahedral carbonyl intermediate
4. aldol
a. only 1 and 2
b. only 1, 3 and 4
c. only 2, 3 and 4
d. 1, 2, 3 and 4

+. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 2
%. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

1-. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an"
11. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

12. )hich of the following compounds can be prepared by an aldol condensation by treating a single
carbonyl compound with base?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" !
1. )hich of the following compounds can be prepared by an aldol condensation by treating a single
carbonyl compound with base?
a. 1
b. 2
c. 3
d. 4

1!. )hich of the following compounds can be prepared by a mixed aldol condensation by treatment of a
mixture of two carbonyl compounds and .a/H?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" &
1&. )hich of the following compounds can be prepared by a mixed aldol condensation by treatment of a
mixture of two carbonyl compounds and .a/H?
a. 1
b. 2
c. 3
d. 4

1$. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

1*. )hat is the ma,or organic product obtained from the following reaction?
'rown Organic Chemistry $e (est 'an" $
a. 1
b. 2
c. 3
d. 4

1+. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

1%. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" *
2-. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

21. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" +
22. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

2. )hat is the ma,or organic product obtained from the following reaction?
'rown Organic Chemistry $e (est 'an" %
a. 1
b. 2
c. 3
d. 4

2!. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

2&. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 1-
2$. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

2*. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 11
2+. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

2%. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

-. )hat is the ma,or organic product obtained from the following reaction?
'rown Organic Chemistry $e (est 'an" 12
a. 1
b. 2
c. 3
d. 4

1. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

2. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 1
. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

!. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 1!
&. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

$. )hat is the ma,or organic product obtained from the following se0uence of reactions?
'rown Organic Chemistry $e (est 'an" 1&
a. 1
b. 2
c. 3
d. 4

*. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

+. )hat is the ma,or organic product obtained from the following reaction?
'rown Organic Chemistry $e (est 'an" 1$
a. 1
b. 2
c. 3
d. 4

%. )hat is the ma,or organic product obtained from the following reaction?
a. 1
b. 2
c. 3
d. 4

!-. )hich one of the following "etones cannot be made 1ia an acetoacetate ester synthesis?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 1*
!1. )hich of the following carboxylic acids can be made 1ia a malonate ester synthesis?
a. 1
b. 2
c. 3
d. 4

!2. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 1+
!. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

!!. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 1%
!&. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

!$. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 2-
!*. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

!+. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 21
!%. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

&-. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 22
&1. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

&2. )hat is the ma,or organic product obtained from the following se0uence of reactions?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 2
&. )hich combination of organic bromide(s) and dicarbonyl compound can be used to prepare the
following product (in a multistep synthesis)?
a. 1
b. 2
c. 3
d. 4

&!. )hich combination of organic bromide(s) and dicarbonyl compound can be used to prepare the
following product (in a multistep synthesis)?
a. 1
b. 2
c. 3
d. 4

'rown Organic Chemistry $e (est 'an" 2!
PROBLEM
1. )hat is the ma,or organic product obtained from the following reaction?

2. )hat is the ma,or organic product obtained from the following reaction?
. )hat is the ma,or organic product obtained from the following reaction?
!. )hat is the ma,or organic product obtained from the following reaction?

&. )hat is the ma,or organic product obtained from the following reaction?

$. )hat is the ma,or organic product obtained from the following reaction?
'rown Organic Chemistry $e (est 'an" 2&

'rown Organic Chemistry $e (est 'an" 2$
*. )hat is the ma,or organic product obtained from the following reaction?

+. )hat is the ma,or organic product obtained from the following reaction?

%. )hat is the ma,or organic product obtained from the following reaction?

1-. )hat is the ma,or organic product obtained from the following se0uence of reactions?


'rown Organic Chemistry $e (est 'an" 2*
12. )hat is the ma,or organic product obtained from the following reaction?

1. )hat is the ma,or organic product obtained from the following reaction?

1!. )hat is the ma,or organic product obtained from the following se0uence of reactions?
1&. )hat is the ma,or organic product obtained from the following se0uence of reactions?

1$. )hat is the ma,or organic product obtained from the following se0uence of reactions?
'rown Organic Chemistry $e (est 'an" 2+