Deck 19: Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Question 1

What is the product of the Dieckmann condensation of this diester,

A) I
B) II
C) III
D) I and II
E) I,II,and III

Answer 1

I and II

Question 2

What would be the product of the following sequence?

A) I
B) II
C) III
D) IV
E) V

Answer 2

I

Question 3

Why is CH₃ONa not used in the Claisen condensation of ethyl acetate?

A) CH₃O^- is a weaker base than the CH₃CH₂O^- which is used.
B) CH₃O^-Na⁺ is more difficult to prepare than CH₃CH₂O^-Na⁺.
C) CH₃O^- would abstract a proton from the ethyl group of the ester.
D) Use of CH₃O^-Na⁺ would result in transesterification.
E) CH₃O^-Na⁺ can be used as well as CH₃CH₂O^-Na⁺.

Answer 3

Use of CH₃O^-Na⁺ would result in transesterification.

Question 4

What is the product of the Dieckmann condensation of this diester,

A) I
B) II
C) III
D) IV
E) V

Question 5

The product(s)of the reaction of 2 mol of ethyl butanoate with sodium ethoxide is(are):

A)

B)

C)

D)

E)

Question 6

Consider the synthesis below: What is compound X?

A) O=C(OEt)₂
B) HCO₂Et
C) EtO-CO-CO-OEt
D) CH₃CO₂Et
E) BrCH₂CO₂Et

Question 7

What is the product of the Dieckmann condensation of this diester,

A) I
B) II
C) III
D) IV
E) V

Question 8

What is the product of the Dieckmann condensation of this diester,

A) I
B) II
C) III
D) IV
E) V

Question 9

Which compound could be prepared via Dieckmann condensation?

A) I
B) II
C) III
D) IV
E) V

Question 10

The Claisen condensation produces which of these?

A) An $\infty$ -keto ester
B) A $\beta$ -keto ester
C) A $\beta$ -hydroxy ester
D) A $\beta$ -hydroxyaldehyde
E) A $\beta$ -diketone

Question 11

Which of the following would afford the best synthesis of diethyl phenylmalonate,

A)

B)

C)

D)

E)

Question 12

The reaction of diethyl heptanedioate with sodium ethoxide would give as the product:

A) I
B) II
C) III
D) IV
E) V

Question 13

The reaction of diethyl hexanedioate with sodium ethoxide would give as the product:

A) I
B) II
C) III
D) IV
E) V

Question 14

What product(s)is (are)likely to be obtained upon Dieckmann condensation of the following substance?

A) I and II
B) II and III
C) III and IV
D) I and III
E) II and IV

Question 15

What is the expected product from the following reaction sequence?

A) I
B) II
C) III
D) IV
E) V

Question 16

What product is formed during the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 17

What would be the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 18

What is the product of the Dieckmann condensation of this diester,

A) I
B) II
C) III
D) IV
E) V

Question 19

Which of these combinations is not one which would result in the formation of essentially one Claisen condensation product when one compound is added slowly to the mixture of the other and the base employed?

A)
HCO₂Et + CH₃CH₂CO₂Et
B) PhCO₂Et + CH₃CO₂Et
C) (CO₂Et)₂ + PhCH₂CO₂Et
D) (CH₃)₃CCO₂Et + CH₃CO₂Et
E) PhCH₂CO₂Et + CH₃CO₂Et

Question 20

Cyclization reactions,such as the Dieckmann condensation,are best carried out using fairly dilute solutions of the compound to be cyclized.Why is this so?

A) It then is possible to use less base.
B) The reagents generally are expensive.
C) A smaller amount of the compound to be cyclized can be used.
D) Intermolecular condensation is minimized at low concentration.
E) The concentration factor is unimportant.

Question 21

Which reagents would you use to prepare the following substance from ethyl acetoacetate?

A) (i)NaH/DMSO;(ii)PhCOCl;(iii)OH ^- /H₂O,heat;(iv)H₃O⁺;(v)heat
B) (i)NaOEt/EtOH;(ii)PhCOCH₂Br;(iii)OH ^- /H₂O,heat;(iv)H₃O⁺;(v)heat
C) i)heat;ii)NaOEt/EtOH;iii)PhCOCH₂Br
D) (i)NaOEt/EtOH;(ii)PhCl
E) (i)NaOEt/EtOH;(ii)PhCOCl;(iii)OH ^- /H₂O,heat;(iv)H₃O⁺;(v)heat

Question 22

What is the product of the Dieckmann-like condensation of this ketoester, IV V

A) I
B) II
C) III
D) IV
E) V

Question 23

The product,C,of the following sequence of reactions, would be:

A)

B)

C)

D)

E)

Question 24

Which of these compounds cannot self-condense in the presence of dilute aqueous alkali?

A) 3-(4-Nitrophenyl)propanal
B) 2-Methyl-3-pentanone
C) 2-(4-Nitrophenyl)propanal
D) 3-(4-Nitrophenyl)-2-butanone
E) All of the above compounds can self-condense.

Question 25

The aldol reaction of cyclohexanone produces which of these self-condensation products?

A) I
B) II
C) III
D) IV
E) V

Question 26

What would be the major product of the following reaction?

A) CH₃CH₂CH₂OH + CH₃CH₂COO^-
B)

C)

D)

E)

Question 27

Predict the product from the following sequence:

A) I
B) II
C) III
D) IV
E) V

Question 28

What would be the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 29

Predict the product from the following sequence:

A) I
B) II
C) III
D) IV
E) V

Question 30

What is the product of the Dieckmann-like condensation of this ketoester,

A) I
B) II
C) III
D) IV
E) V

Question 31

What would be the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 32

Predict the product from the following sequence:

A) I
B) II
C) III
D) IV
E) V

Question 33

What product(s)result from the Claisen condensation carried out with an equimolar mixture of ethyl acetate and ethyl propanoate?

A) I
B) II
C) III
D) IV
E) All of these

Question 34

The aldol reaction of cyclohexanone produces which of these self-condensation products?

A) I
B) II
C) III
D) IV
E) V

Question 35

Which of these is not a reversible process?

A) Base-promoted ester hydrolysis
B) Acid-catalyzed ester hydrolysis
C) Aldol addition
D) Claisen condensation
E) Acetal formation

Question 36

What is the product of the Dieckmann-like condensation of this ketoester,

A) I
B) II
C) III
D) IV
E) V

Question 37

Which is the only one of these compounds which cannot self-condense in the presence of dilute aqueous alkali?

A) Phenylethanal
B) Propanal
C) 2-Methylpropanal
D) 3-Methylpentanal
E) 2,2-Dimethylpropanal

Question 38

What is the product of the Dieckmann-like condensation of this ketoester,

A) I
B) II
C) III
D) IV
E) V

Question 39

What would be the major product of the following reaction?

A)

B)

C)

D)

E)

Question 40

The aldol condensation product formed from 3-pentanone in the presence of base has the IUPAC name:

A) 5-Ethyl-4-methyl-4-hepten-3-one
B) 5-Ethyl-4-methyl-5-hepten-3-one
C) 4-Methyl-4-nonen-3,7-dione
D) 3-Ethyl-4-methyl-3-hepten-5-one
E) 3-Ethyl-4-methyl-2-hepten-5-one

Question 41

What would be the final product of the following reaction sequence?

A) C₆H₅CH₂CH₂CH₂CH₃
B)

C)

D)

E)

Question 42

What would be the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 43

Which reagents would you use to synthesize this compound by an aldol condensation?

A)

B)

C)

D)

E)

Question 44

What would be the major product,B,of the following reaction sequence?

A) I
B) II
C) III
D) IV
E) V

Question 45

Which of these compounds can react with 4-methylhexanal to afford good yields of the crossed aldol product?

A) 3-(4-Nitrophenyl)propanal
B) 2-Methyl-3-pentanone
C) 2-(4-Nitrophenyl)propanal
D) 3-(4-Nitrophenyl)-2-butanone
E) None of the above compounds will give good yields of the crossed aldol product with 4-methylhexanal.

Question 46

The retro-aldol reaction of gives:

A)

B)

C)

D)

E)

Question 47

What would be the product,B,of the following reaction sequence?

A) C₆H₅CH=CHCO₂H
B)

C) C₆H₅CH₂CH₂CO₂H
D)

E)

Question 48

What would be the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 49

Consider the synthesis above in answering this question.What is compound A?

A) Butanone
B) Butanal
C) Propanal
D) 1-Butanol
E) 2-Methylpropanal

Question 50

What would be the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 51

What would be the major product,B,of the following reaction sequence?

A) I
B) II
C) III
D) IV
E) V

Question 52

Which of these is not among the reaction products when a crossed aldol addition occurs between ethanal and butanal?

A)

B)

C)

D)

E)

Question 53

What would be the major product,B,of the following reaction sequence?

A) I
B) II
C) III
D) IV
E) V

Question 54

What is the intermediate B in the synthesis shown above?

A) I
B) II
C) III
D) IV
E) V

Question 55

What would be the product,C,of the following reaction sequence?

A) (CH₃)₃CCH₂CH₂CH₂OH
B)

C)

D)

E)

Question 56

What would be the product,C,of the following reaction sequence?

A) (CH₃)₃CCH₂CH₂CH₂OH
B)

C)

D)

E)

Question 57

Consider the synthesis above in answering this question.What is compound A?

A) Butanone
B) Butanal
C) Propanal
D) 1-Butanol
E) 2-Methylpropanal

Question 58

If butanal is added slowly to an aqueous solution of sodium hydroxide and 2,2-dimethylpropanal at 25 $\degree$ C,the principal product is which of these?

A)

B)

C)

D)

E)

Question 59

Which of these compounds can react with 4-methylpentanal to afford good yields of the crossed aldol product?

A) 3-(4-Nitrophenyl)propanal
B) 2-Ethyl-2-methylheptanal
C) 2-(4-Nitrophenyl)propanal
D) 3-(4-Nitrophenyl)-2-butanone
E) None of the above compounds will give good yields of the crossed aldol product with 4-methylhexanal.

Question 60

What is the intermediate B in the synthesis shown above?

A) I
B) II
C) III
D) IV
E) V

Question 61

When cyclizes in basic solution,which of these compounds will be formed?

A) I
B) II
C) III
D) IV
E) V

Question 62

What product results from the intramolecular aldol reaction of 2,5-hexanedione?

A) I
B) II
C) III
D) IV
E) V

Question 63

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 64

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 65

What is the missing reagent?

A)

B)

C)

D)

E)

Question 66

What is the major product of the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 67

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 68

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 69

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 70

The reaction of with base affords which of these products?

A) I
B) II
C) III
D) IV
E) V

Question 71

What would be the product,C,of the following reaction sequence?

A)

B)

C)

D)

E)

Question 72

What compound results from the aldol cyclization of

A) I
B) II
C) III
D) IV
E) Both III and IV

Question 73

What product is formed during the following reaction?

A) I
B) II
C) III
D) IV
E) V

Question 74

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 75

The product of the following reaction is:

A) I
B) II
C) III
D) IV
E) V

Question 76

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 77

What starting compound(s)would you use in an aldol reaction to prepare

A) I
B) II
C) III
D) IV
E) V

Question 78

The aldol cyclization of produces which of these?

A) I
B) II
C) III
D) IV
E) V

Question 79

What starting compound(s)would you use in an aldol reaction to prepare as the major product:

A) I
B) II
C) III
D) IV
E) V

Question 80

What would be the product,C,of the following reaction sequence?

A)

B)

C)

D)

E)
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