Deck 17: Aldehydes and Ketones Ii Aldol Reactions

Question 1

Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?

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

Answer 1

V

Question 2

Which compound would be the weakest acid?

A) CHCl₂CH₂CH₂CO₂H
B) ClCH₂CHClCH₂CO₂H
C) CH₃CCl₂CH₂CO₂H
D) CH₃CHClCHClCO₂H
E) CH₃CH₂CCl₂CO₂H

Answer 2

CHCl₂CH₂CH₂CO₂H

Question 3

What is the IUPAC name for

A) "2,3-0Dimethylbutyl acetate"
B) "2,3-Dimethyl-4-oxoethanal"
C) "2,3-Dimethylbutyl methanoate"
D) "2,3-Dimethylbutyl methylate"
E) "2,3-Dimethylbutyl formylate"

Answer 3

"2,3-Dimethylbutyl methanoate"

Question 4

Which compound would be the strongest acid?

A) CHCl₂CH₂CH₂CO₂H
B) ClCH₂CHClCH₂CO₂H
C) CH₃CCl₂CH₂CO₂H
D) CH₃CHClCHClCO₂H
E) CH₃CH₂CCl₂CO₂H

Question 5

The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm^-1 and a sharp band at 1710 cm^-1.Which of these compounds could it be?

A) 1-Butanol
B) Propyl acetate
C) Butanoic acid
D) Acetyl chloride
E) Acetic anhydride

Question 6

Which of the following would be the strongest acid?

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

Question 7

Which of the following would be the strongest acid?

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

Question 8

What is the IUPAC name for

A) " $\infty$ -Chlorovaleryl chloride"
B) "2-Chloropentanoyl chloride"
C) "1-Chloropentanoyl chloride"
D) "1,2-Dichloropentanal"
E) "1-Chloro-1-butanecarbonyl chloride"

Question 9

Which of the following would be the strongest acid?

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

Question 10

Which of the following would be the weakest acid?

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

Question 11

In which of the following sequences are the compounds listed in order of decreasing acidity?

A) PhCOOH > H₂O > PhOH > PhCH₂OH > PhH
B) PhCOOH > PhOH > H₂O > PhCH₂OH > PhH
C) PhH > H₂O > PhOH > PhCH₂OH > PhCOOH
D) PhOH > H₂O > PhCOOH > PhCH₂OH > PhH
E) PhCOOH > H₂O > PhOH > PhH > PhCH₂OH

Question 12

In which of the following sequences are the compounds listed in order of increasing acidity?

A) NH₃ < HC $\equiv$ CH < CH₃CH₂OH < H₂O < CH₃COOH
B) CH₃CH₂OH < NH₃ < H₂O < HC $\equiv$ CH < CH₃COOH
C) CH₃COOH < CH₃CH₂OH < H₂O < NH₃ < HC $\equiv$ CH
D) H₂O < CH₃COOH < CH₃CH₂OH < HC $\equiv$ CH < NH₃
E) NH₃ < H₂O < CH₃COOH < HC $\equiv$ CH < CH₃CH₂OH

Question 13

Which of the following would be the weakest acid?

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

Question 14

Which of the following would be the strongest acid?

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

Question 15

Which of the following would be the strongest acid?

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

Question 16

Which of the following would be the strongest acid?

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

Question 17

Which of the following is the best name for the following compound?

A) Isobutyl ethanoate
B) Ethyl isopropanoate
C) 3-methylbutyl ethanoate
D) Ethoxy isobutyl ketone
E) Ethyl 3-methylbutanoate

Question 18

The correct structure for ethyl 3-methylbutanoate is:

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

Question 19

In which of the following sequences are the compounds listed in order of decreasing acidity?

A) CH₃COOH > H₂O > CH₃CH₂OH > HC $\equiv$ CH > NH₃
B) CH₃CH₂OH > CH₃COOH > H₂O > HC $\equiv$ CH > NH₃
C) CH₃COOH > CH₃CH₂OH > H₂O > NH₃ > HC $\equiv$ CH
D) H₂O > CH₃COOH > CH₃CH₂OH > HC $\equiv$ CH > NH₃
E) CH₃CH₂OH > H₂O > CH₃COOH > HC $\equiv$ CH > NH₃

Question 20

In which of the following sequences are the compounds listed in order of decreasing acidity?

A) CH₃COOH > H₂O > PhOH > HC $\equiv$ CH > NH₃
B) PhOH > CH₃COOH > H₂O > HC $\equiv$ CH > NH₃
C) CH₃COOH > PhOH > H₂O > HC $\equiv$ CH > NH₃
D) H₂O > CH₃COOH > PhOH > HC $\equiv$ CH > NH₃
E) PhOH > H₂O > CH₃COOH > HC $\equiv$ CH > NH₃

Question 21

Which of the following acids would have the smallest value for pK_a1?

A) HOOCCH₂CH₂CH₂CH₂CH₂COOH
B) HOOCCH₂CH₂CH₂CH₂COOH
C) HOOCCH₂CH₂CH₂COOH
D) HOOCCH₂CH₂COOH
E) HOOCCH₂COOH

Question 22

Which of the following would be the strongest acid?

A) Benzoic acid
B) 4-Nitrobenzoic acid
C) 4-Methylbenzoic acid
D) 4-Methoxybenzoic acid
E) 4-Iodobenzoic acid

Question 23

Which of the following would be the strongest acid?

A) 2,3-Dimethylhexanoic acid
B) 3,3-Diiodopentanoic acid
C) 3-Iodo-4-bromopentanoic acid
D) 3-Chloro-4-bromohexanoic acid
E) 2-Fluoro-4-bromopentanoic acid

Question 24

Which of the following acids would have the largest value for pK_a?

A) BrCH₂CH₂CH₂COOH
B) ClCH₂CH₂CH₂COOH
C) Cl₂CHCH₂CH₂COOH
D) ICHBrCH₂CH₂COOH
E) BrCCl₂CH₂CH₂COOH

Question 25

Which compound would be most acidic?

A) Acetic acid
B) Ethanol
C) Phenol
D) Acetone
E) Water

Question 26

A compound has the molecular formula C₈H₁₄O₄.Its IR spectrum shows a strong absorption band near 1740 cm^-1.Its ¹H NMR spectrum consists of: triplet,
$\delta$ 1.3
Singlet,
$\delta$ 2.6
Quartet,
$\delta$ 4.2
The most likely structure for the compound is:

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

Question 27

A compound has the molecular formula,C₆H₁₂O₂.Its IR spectrum shows a strong absorption band near 1740 cm^-1;its ¹H NMR spectrum consists of two singlets,at $\delta$ 1.4 and $\delta$ 2.0.The most likely structure for this compound is:

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

Question 28

Which of the following acids would have the smallest value for pK_a?

A) BrCH₂CH₂CH₂COOH
B) ClCH₂CH₂CH₂COOH
C) Cl₂CHCH₂CH₂COOH
D) ICHBrCH₂CH₂COOH
E) BrCCl₂CH₂CH₂COOH

Question 29

A compound with the molecular formula C₁₈H₁₈O₄ has a ¹H NMR spectrum that consists of: singlet,
$\delta$ 2.7
Singlet,
$\delta$ 3.1
Multiplet,
$\delta$ 7.3
The IR spectrum shows a strong absorption band near 1750 cm^-1.The most likely structure for the compound is:

A)

B)

C)

D)

E)

Question 30

Predict the major organic product of the reaction sequence below:

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

Question 31

Which of the following would be the weakest acid?

A) Benzoic acid
B) 4-Nitrobenzoic acid
C) 4-Methylbenzoic acid
D) 4-Methoxybenzoic acid
E) 4-Iodobenzoic acid

Question 32

A compound has the molecular formula,C₆H₁₂O₂.Its IR spectrum shows a strong absorption band near 1740 cm^-1;its ¹H NMR spectrum consists of two singlets,at $\delta$ 1.2 and $\delta$ 3.6.The most likely structure for this compound is:

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

Question 33

Which of the following would be the weakest acid?

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

Question 34

What is the reactant of the following reaction sequence?

A) HCO₂CH₂C₆H₅
B) C₆H₅CH₂COOH
C) C₆H₅CH₂Cl
D) C₆H₅CHClCOOH
E) O=C(CH₂C₆H₅)₂

Question 35

A compound with the molecular formula C₅H₁₀O₂ gave the following ¹H NMR spectrum: triplet,
$\delta$ 0.90
Multiplet,
$\delta$ 1.60
Singlet,
$\delta$ 1.95
Triplet,
$\delta$ 3.95
The IR spectrum showed a strong absorption band near 1740 cm^-1.The most likely structure for the compound is:

A)

B)

C)

D)

E)

Question 36

In which of these species are all the carbon-oxygen bonds of equal length?

A) Diethyl carbonate
B) Methyl butanoate
C) Lithium acetate
D) Propionic anhydride
E) Pentanoic acid

Question 37

In which of the following are the compounds listed in order of decreasing acidity?

A) CH₃CO₂H > CH₃CH₂OH > C₆H₅OH > H₂O
B) C₆H₅OH > CH₃CO₂H > H₂O > CH₃CH₂OH
C) CH₃CO₂H > H₂O > C₆H₅OH > CH₃CH₂OH
D) H₂O > CH₃CO₂H > C₆H₅OH > CH₃CH₂OH
E) None of the above

Question 38

Which compound would be most acidic?

A)

B)

C)

D)

E)

Question 39

In which of the following are the compounds listed in order of decreasing acidity?

A) CH₃CO₂H > CH₃CH₂OH > C₆H₅OH > H₂O
B) C₆H₅OH > CH₃CO₂H > H₂O > CH₃CH₂OH
C) CH₃CO₂H > H₂O > C₆H₅OH > CH₃CH₂OH
D) H₂O > CH₃CO₂H > C₆H₅OH > CH₃CH₂OH
E) CH₃CO₂H > C₆H₅OH > CH₃CH₂OH > H₂O

Question 40

What is the expected product,A,of the following reaction sequence?

A) HCO₂CH₂C₆H₅
B) C₆H₅CH₂COOH
C) C₆H₅CH₂OSO₃H
D) C₆H₅CHClCOOH
E) O=C(CH₂C₆H₅)₂

Question 41

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

A) C₆H₅CH₂CH₂CO₂H
B) C₆H₅CH₂CH₂NH₂
C) C₆H₅CH₂CH(CH₃)CN
D) C₆H₅CH₂CH=NH
E) C₆H₅CH₂NH₂

Question 42

What is the expected product,A,of the following reaction sequence?

A) Benzyl formate
B) Phenylacetic acid
C) Benzenesulfonic acid
D) 1-chloro-1-phenyl acetic acid
E) Dibenzylketone

Question 43

Reasoning by analogy,one would predict that the reaction of carbon disulfide with sec-butylmagnesium bromide should yield which of the following (after acidification)?

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

Question 44

Alkaline hydrolysis of an ester involves initial attack by hydroxide ion on the carbonyl carbon.The presence of substituents on the aromatic ring of ethyl benzoate may be expected to increase/decrease the rate of hydrolysis of this ester.In what order should the five substituents below be arranged to represent the decreasing order of the rates of hydrolysis when these substituents are present in the para- position of the aromatic ring in ethyl benzoate?

A) -NO₂ > -H > -Cl > -CH₃ > -OCH₃
B) -NO₂ > -Cl > -H > -CH₃ > -OCH₃
C) -OCH₃ > -CH₃ > -Cl > -H > -NO₂
D) -Cl > -NO₂ > -H > -OCH₃ > -CH₃
E) -H > -Cl > -CH₃ > -OCH₃ > -NO₂

Question 45

What would be the final product,F,of the following sequence of reactions?

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

Question 46

What would be the product of the following reaction ? \

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

Question 47

An acid chloride is prepared from the related carboxylic acid by reaction with which of these?

A) HCl
B) Cl₂
C) SOCl₂
D) HOCl
E) AlCl₃

Question 48

Which compound would be most reactive toward nucleophilic acyl addition-elimination?

A) CH₃CO₂Na
B) CH₃COCl
C) (CH₃CO)₂O
D) CH₃CONH₂
E) CH₃CO₂CH₃

Question 49

What is the reactant of the following reaction sequence?

A) BrCH₂C₆H₅
B) C₆H₅CH₂COOH
C) C₆H₅CH₂OH
D) C₆H₅CH₂CH₂COOH
E) O=C(CH₂C₆H₅)₂

Question 50

What would be the final product,F,of the following sequence of reactions?

A) 1-Bromo-2-methyl propane
B) 3-Bromo-3-methylbutanoic acid
C) Butanoic acid
D) 3-Methylbutanoic acid
E) Methyl 2-methylproanoate

Question 51

What is the expected product,A,of the following reaction sequence?

A) HCO₂CH₂C₆H₅
B) C₆H₅CH₂COOH
C) C₆H₅CH₂OSO₃H
D) C₆H₅CHClCOOH
E) O=C(CH₂C₆H₅)₂

Question 52

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

A) 2,2-Dimethylpropanoic acid
B) Methyl 2,2-dimethylpropanoate
C) 2,2-Dimethyl-1-propanol
D) t-Butyl methyl ether
E) 3,3-Dimethyl-2-butanone

Question 53

Which of the following will not undergo hydrolysis,whether acid or base is present?

A) CH₃COCl
B) CH₃CONH₂
C) (CH₃CO)₂O
D) CH₃CO₂CH₂CH₃
E) CH₃COCH₂CH₂CH₃

Question 54

The relative reactivity of acyl compounds toward nucleophilic acyl addition-elimination is:

A) Amide > ester > acid anhydride > acyl chloride
B) Acyl chloride > ester > acid anhydride > amide
C) Ester > acyl chloride > acid anhydride > amide
D) Acyl chloride > acid anhydride > ester > amide
E) Acid anhydride > acyl chloride > ester > amide

Question 55

Which of these combinations will not produce benzoic acid?

A) C₆H₅CH₂OH + KMnO₄/OH ^- /H₂O,heat;then H₃O⁺
B) C₆H₅CH₃ + KMnO₄/OH ^- /H₂O,heat;then H₃O⁺
C) C₆H₆ + CO₂,high pressure
D) C₆H₅COCH₃ + Cl₂/OH ^- /H₂O;then H₃O⁺
E) C₆H₅COCl + OH ^- /H₂O;then H₃O⁺

Question 56

Choose the reagent(s)that would bring about the following reaction: CH₃CH₂CH₂COCl -- $\rightarrow$ CH₃CH₂CH₂CHO

A) H₂/Ni
B) Li/liq NH₃
C) LiAl(OC(CH₃)₃)₃H
D) NaBH₄,CH₃OH
E) LiAlH₄,ether

Question 57

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

A) (CH₃)₃CCO₂H
B) (CH₃)₃CCOCH₃
C) (CH₃)₃CCH₂OH
D) (CH₃)₃COCH₃
E) (CH₃)₃CCO₂CH₃

Question 58

What would be the final product,F,of the following sequence of reactions?

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

Question 59

Which of these compounds could not be formed by nucleophilic attack by an appropriate reagent on acetyl chloride?

A) CH₃CONH₂
B) CH₃CO₂CH₂CH₃
C) ClCH₂COCl
D) CH₃CO₂H
E) (CH₃CO)₂O

Question 60

Which of these combinations will not produce benzoic acid?

A) C₆H₅CH₂OH + KMnO₄/OH ^- /H₂O,heat;then H₃O⁺
B) C₆H₅CH₃ + KMnO₄/OH ^- /H₂O,heat;then H₃O⁺
C) C₆H₆ + CO₂,high pressure
D) C₆H₅COCH₃ + I₂/OH ^- /H₂O;then H₃O⁺
E) C₆H₅COCl + OH ^- /H₂O;then H₃O⁺

Question 61

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

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

Question 62

The product of the following reaction is:

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

Question 63

Predict the major organic product of the reaction sequence,

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

Question 64

Which of the following compounds is capable of forming a $\delta$ -lactone?

A) 5-Hydroxypentanoic acid
B) Pentanedioic acid
C) 4-Hydroxypentanoic acid
D) 3-Hydroxypentanoic acid
E) 2-Hydroxypentanoic acid

Question 65

The product,Z,of the following sequence of reactions is which compound?

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

Question 66

Predict the final product likely to be obtained when (S)-2-methyl-3-pentanol is subjected to the following sequence of reactions: i)benzoyl chloride;ii)NaOH (aq),heat .

A) (S)-2-methyl-3-pentanol
B) (R)-2-methyl-3-pentanol
C) (R,S)-2-methyl-3-pentanol
D) 2-Methyl-2-pentene
E) (R,S)-2-methyl-3-pentanol and 2-methyl-2-pentene in more or less equal amounts

Question 67

Intramolecular dehydration to form a cyclic monoester is most likely to occur when which of the following is heated with acid?

A) CH₃CH₂CH₂CHOHCO₂H
B) CH₃CH₂CHOHCH₂CO₂H
C) CH₃CH₂CH₂CH₂CO₂H
D) CH₃CHOHCH₂CH₂CO₂H
E) HO₂CCH₂CH₂CO₂H

Question 68

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

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

Question 69

Choose the reagent(s)that would bring about the following reaction: CH₃CH₂CH₂CO₂CH₃ -- $\rightarrow$ CH₃CH₂CH₂CHO

A) H₂/Ni
B) Li/liq NH₃
C)

D) NaBH₄,CH₃OH
E) LiAlH₄,ether

Question 70

Which of the following is not a method for preparing butanoic acid?

A) CH₃CH₂CH₂Br + NaCN;then H₃O⁺,reflux
B) CH₃CH₂CH₂MgBr + CO₂;then H₃O⁺
C) CH₃CH₂CH₂OH + CO
D) CH₃CH₂CH₂CO₂Et + OH ^- /H₂O;then H₃O⁺
E) CH₃CH₂CH₂CH₂OH + KMnO₄/OH ^- /H₂O/heat;then H₃O⁺

Question 71

Which of the following would serve as a reasonable synthesis of ethyl benzoate?

A)

B)

C)

D) All of the above
E) None of the above

Question 72

What is the product of this reaction?

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

Question 73

Which of the following reactions would constitute a reasonable synthesis of propyl acetate?

A)

B)

C)

D) All of these
E) None of these

Question 74

Which of the following combinations of reagents would not produce an ester?

A)

B)

C)

D)

E)

Question 75

Which of the following would yield (S)-2-butanol?

A)

B)

C)

D) All of these
E) None of these

Question 76

Predict the major organic product,P,of the following sequence of reactions:

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

Question 77

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

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

Question 78

$\gamma$ - And $\delta$ -hydroxy acids can be esterified intramolecularly to form compounds known as which of these?

A) Anhydrides
B) Cycloalkenes
C) Lactones
D) Lactams
E) Cyclic ketones

Question 79

What is the product of this reaction?

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

Question 80

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

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