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Why is the enolate of acetone less basic than the allyl anion derived from propene?


A) Because there are more atoms in acetone
B) Because there are more resonance structures for the enolate of acetone
C) It isn't; the allyl anion is less basic.
D) One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen.

E) A) and C)
F) A) and D)

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Select the appropriate sequence of reactions to accomplish the following synthesis. Select the appropriate sequence of reactions to accomplish the following synthesis. A) [1] Br<sub>2</sub>, CH<sub>3</sub>CO<sub>2</sub>H; [2] Li<sub>2</sub>CO<sub>3</sub>, LiBr, DMF; [3] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br B) [1] Br<sub>2</sub>, CH<sub>3</sub>CO<sub>2</sub>H; [2] Mg, Et<sub>2</sub>O; [3] CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br C) [1] LDA; [2] BrCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br; [3] NaOEt D) [1] NaOEt; [2] BrCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br; [3] LDA


A) [1] Br2, CH3CO2H; [2] Li2CO3, LiBr, DMF; [3] CH3CH2CH2CH2Br
B) [1] Br2, CH3CO2H; [2] Mg, Et2O; [3] CH3CH2CH2CH2Br
C) [1] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt
D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA

E) A) and B)
F) B) and C)

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Which of the following four compounds is the most acidic? Which of the following four compounds is the most acidic? A) I B) II C) III D) IV


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

E) C) and D)
F) B) and D)

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Which of the following ketones will give a positive iodoform test?


A) 3-Heptanone
B) 2-Pentanone
C) 3-Hexanone
D) Cyclohexanone

E) None of the above
F) A) and D)

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Why can't you prepare 2-tert-butylcyclohexanone by the following reaction? Why can't you prepare 2-tert-butylcyclohexanone by the following reaction? A) Because tert-butyl bromide is too basic. B) Because tert-butyl bromide cannot undergo an S<sub>N</sub>2 reaction. C) Because tert-butyl bromide is a nucleophile. D) Because tert-butyl bromide is not a stable compound.


A) Because tert-butyl bromide is too basic.
B) Because tert-butyl bromide cannot undergo an SN2 reaction.
C) Because tert-butyl bromide is a nucleophile.
D) Because tert-butyl bromide is not a stable compound.

E) A) and B)
F) A) and C)

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Which is the thermodynamic enolate of 2-methylcyclohexanone? Which is the thermodynamic enolate of 2-methylcyclohexanone? A) I B) II C) III D) IV


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

E) All of the above
F) A) and B)

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If you want to form a thermodynamic enolate, you want to:


A) Keep the reaction as cold as possible.
B) Use an aprotic solvent such as THF.
C) Use a protic solvent such as ethanol.
D) Use a carboxylic acid.

E) A) and B)
F) A) and C)

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Why is it difficult to stop the halogenation of ketones under basic conditions at the mono-halogenated stage?


A) The ketone undergoes a Bayer-Villigar oxidation.
B) The ketone is reduced.
C) The ketone undergoes an Aldol reaction.
D) The bromine helps to stabilize the second enolate, making the product more acidic than the starting material.

E) A) and C)
F) A) and B)

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What is the starting material required to accomplish the following transformation? What is the starting material required to accomplish the following transformation? A) I B) II C) III D) IV


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

E) None of the above
F) A) and C)

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What is the major product of the following reaction? What is the major product of the following reaction? A) I B) II C) III D) IV


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

E) None of the above
F) A) and D)

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A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with


A) bromine with acetic acid.
B) bromine and aqueous hydroxide ion.
C) THF, LDA at -78 °C followed by reaction with bromine.
D) base and methyl bromide.

E) C) and D)
F) B) and D)

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What is the product of the following reaction? What is the product of the following reaction? A) I B) II C) III D) IV


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

E) C) and D)
F) A) and C)

Correct Answer

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What is the missing reagent for the following reaction? What is the missing reagent for the following reaction? A) Br<sub>2</sub>/HOAc B) Br<sub>2</sub>/KOH C) Cl<sub>2</sub>/FeCl<sub>3</sub> D) Br<sub>2</sub>/FeBr<sub>3</sub>


A) Br2/HOAc
B) Br2/KOH
C) Cl2/FeCl3
D) Br2/FeBr3

E) B) and C)
F) A) and D)

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Which is the more stable form of acetophenone? Which is the more stable form of acetophenone? A) Only I B) Only II C) Only III D) I and II are equally stable


A) Only I
B) Only II
C) Only III
D) I and II are equally stable

E) B) and D)
F) C) and D)

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Which of the following are enol forms of ethyl acetoacetate drawn below? Which of the following are enol forms of ethyl acetoacetate drawn below? A) Only I B) Only II C) Only III D) I, II, and III


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

E) A) and B)
F) A) and C)

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What is (are) the product(s) of the following reaction? What is (are) the product(s) of the following reaction? A) Only I B) Only II C) Only III D) Only I and III


A) Only I
B) Only II
C) Only III
D) Only I and III

E) None of the above
F) A) and D)

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For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound. This is due largely to what?


A) The C=O bond is much stronger than the C=C bond.
B) The C=C bond is much stronger than the C=O bond.
C) The keto form can undergo intramolecular hydrogen bonding.
D) The enol form can undergo intramolecular hydrogen bonding.

E) All of the above
F) B) and D)

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What is the product of the following reaction? What is the product of the following reaction? A) I B) II C) III D) IV


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

E) C) and D)
F) B) and D)

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Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X (C7H14O) as the major product. X shows a strong absorption in the IR spectrum at 1713 cm-1, and its 1H NMR data is given below. What is the structure of X? Treatment of 2-hexanone with NaOCH<sub>2</sub>CH<sub>3</sub> followed by CH<sub>3</sub>Br affords compound X (C<sub>7</sub>H<sub>14</sub>O) as the major product. X shows a strong absorption in the IR spectrum at 1713 cm<sup>-1</sup>, and its <sup>1</sup>H NMR data is given below. What is the structure of X? \begin{array}{|l|l|l|l|} \hline \text { Signal } & \text { Shift } & \text { Multiplicity } & \text { Integration } \\ & (\mathbf{p p m}) & \\ \hline 1 & 0.96 & \text { triplet } & 3 \mathrm{H} \\ \hline 2 & 1.16 & \text { doublet } & 3 \mathrm{H} \\ \hline 3 & 1.33 & \text { multiplet } & 2 \mathrm{H} \\ \hline 4 & 1.53 & \text { multiplet } & 2 \mathrm{H} \\ \hline 5 & 2.09 & \text { singlet } & 3 \mathrm{H} \\ \hline 6 & 2.52 & \text { multiplet } & 1 \mathrm{H} \\ \hline \end{array} A) I B) II C) III D) IV  Signal  Shift  Multiplicity  Integration (ppm) 10.96 triplet 3H21.16 doublet 3H31.33 multiplet 2H41.53 multiplet 2H52.09 singlet 3H62.52 multiplet 1H\begin{array}{|l|l|l|l|}\hline \text { Signal } & \text { Shift } & \text { Multiplicity } & \text { Integration } \\& (\mathbf{p p m}) & \\\hline 1 & 0.96 & \text { triplet } & 3 \mathrm{H} \\\hline 2 & 1.16 & \text { doublet } & 3 \mathrm{H} \\\hline 3 & 1.33 & \text { multiplet } & 2 \mathrm{H} \\\hline 4 & 1.53 & \text { multiplet } & 2 \mathrm{H} \\\hline 5 & 2.09 & \text { singlet } & 3 \mathrm{H} \\\hline 6 & 2.52 & \text { multiplet } & 1 \mathrm{H} \\\hline\end{array} Treatment of 2-hexanone with NaOCH<sub>2</sub>CH<sub>3</sub> followed by CH<sub>3</sub>Br affords compound X (C<sub>7</sub>H<sub>14</sub>O) as the major product. X shows a strong absorption in the IR spectrum at 1713 cm<sup>-1</sup>, and its <sup>1</sup>H NMR data is given below. What is the structure of X? \begin{array}{|l|l|l|l|} \hline \text { Signal } & \text { Shift } & \text { Multiplicity } & \text { Integration } \\ & (\mathbf{p p m}) & \\ \hline 1 & 0.96 & \text { triplet } & 3 \mathrm{H} \\ \hline 2 & 1.16 & \text { doublet } & 3 \mathrm{H} \\ \hline 3 & 1.33 & \text { multiplet } & 2 \mathrm{H} \\ \hline 4 & 1.53 & \text { multiplet } & 2 \mathrm{H} \\ \hline 5 & 2.09 & \text { singlet } & 3 \mathrm{H} \\ \hline 6 & 2.52 & \text { multiplet } & 1 \mathrm{H} \\ \hline \end{array} A) I B) II C) III D) IV


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

E) A) and B)
F) A) and C)

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Which is the most acidic proton in the following compound? Which is the most acidic proton in the following compound? A) I B) II C) III D) IV


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

E) None of the above
F) All of the above

Correct Answer

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