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Which of the following organic molecules will undergo decarboxylation to form an amine?


A) Histidine
B) Isoamyl acetate
C) Ethyl acetoacetate
D) Pyridine

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

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The following molecule is called The following molecule is called A) an ethyl acetoacetate. B) a 1,3-diketopentanoate. C) a b-keto ester. D) a diethyl malonate.


A) an ethyl acetoacetate.
B) a 1,3-diketopentanoate.
C) a b-keto ester.
D) a diethyl malonate.

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

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C

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


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

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

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C

Starting with cyclohexanone, how could you prepare the diketone below? Starting with cyclohexanone, how could you prepare the diketone below? A) Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone. B) Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone. C) Treat cyclohexanone with a base under thermodynamic conditions. D) Hydrogenate cyclohexanone with Raney nickel.


A) Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone.
B) Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.
C) Treat cyclohexanone with a base under thermodynamic conditions.
D) Hydrogenate cyclohexanone with Raney nickel.

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

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


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

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

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Which of the following compound would most likely undergo racemization under basic conditions?


A) (S) -4-Iodo-2-pentanone
B) (R) -5-Iodo-5-bromo-2-pentanone
C) (R) -3-Iodo-2-pentanone
D) (R) -4-Iodo-2-pentanone

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

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C

Which of the following is the least acidic compound? Which of the following is the least acidic compound? A) II B) I C) III D) IV


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

E) C) and D)
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] LDA; [2] BrCH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>Br; [3] NaOEt B) [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 C) [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 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] LDA; [2] BrCH2CH2CH2CH2Br; [3] NaOEt
B) [1] Br2, CH3CO2H; [2] Li2CO3, LiBr, DMF; [3] CH3CH2CH2CH2Br
C) [1] Br2, CH3CO2H; [2] Mg, Et2O; [3] CH3CH2CH2CH2Br
D) [1] NaOEt; [2] BrCH2CH2CH2CH2Br; [3] LDA

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

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


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

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) IV B) I C) III D) II


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

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

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The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation. The reaction below is a direct enolate alkylation. It has been found that this reaction only works well with unhindered methyl and 1° alkyl halides. Pick the statement that best explains this observation. A) Hindered alkyl halides do not undergo S<sub>N</sub>1 reactions. B) The nucleophilic enolate requires a reaction center that has a positive charge. C) Hindered alkyl halides do not undergo S<sub>N</sub>2 reactions. D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.


A) Hindered alkyl halides do not undergo SN1 reactions.
B) The nucleophilic enolate requires a reaction center that has a positive charge.
C) Hindered alkyl halides do not undergo SN2 reactions.
D) Methyl and 1° alkyl halides can form carbocations that can readily react with the nucleophilic enolate.

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

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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}{llcc} \text {Signal \# } & \text { Shift (ppm) } & \text {Multiplicity } & \text {Integration }\\ 1&0.96& \text {triplet}&3 \mathrm{H}\\ 2&1.16& \text {doublet}&3 \mathrm{H}\\ 3&1.33& \text {multiplet}&2 \mathrm{H}\\ 4&1.53&\text {multiplet}&2 \mathrm{H}\\ 5&2.09& \text {singlet}&3 \mathrm{H}\\ 6&2.52& \text {multiplet}&1 \mathrm{H} \end{array} A) IV B) III C) II D) I Signal #  Shift (ppm)  Multiplicity Integration 10.96triplet3H21.16doublet3H31.33multiplet2H41.53multiplet2H52.09singlet3H62.52multiplet1H\begin{array}{llcc} \text {Signal \# } & \text { Shift (ppm) } & \text {Multiplicity } & \text {Integration }\\1&0.96& \text {triplet}&3 \mathrm{H}\\2&1.16& \text {doublet}&3 \mathrm{H}\\3&1.33& \text {multiplet}&2 \mathrm{H}\\4&1.53&\text {multiplet}&2 \mathrm{H}\\5&2.09& \text {singlet}&3 \mathrm{H}\\6&2.52& \text {multiplet}&1 \mathrm{H}\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}{llcc} \text {Signal \# } & \text { Shift (ppm) } & \text {Multiplicity } & \text {Integration }\\ 1&0.96& \text {triplet}&3 \mathrm{H}\\ 2&1.16& \text {doublet}&3 \mathrm{H}\\ 3&1.33& \text {multiplet}&2 \mathrm{H}\\ 4&1.53&\text {multiplet}&2 \mathrm{H}\\ 5&2.09& \text {singlet}&3 \mathrm{H}\\ 6&2.52& \text {multiplet}&1 \mathrm{H} \end{array} A) IV B) III C) II D) I


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

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

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