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What is the product,Z,of the following reaction sequence? What is the product,Z,of the following reaction sequence? A) I B) II C) III D) IV E) V


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

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Which of these halides is predicted to alkylate malonic ester (as the anion) in highest yield?


A) CH3I
B) C6H5Br
C) (CH3) 3CCH2Cl
D) CH3CHClCH3
E) All of these choices should be equally effective.

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Alkylation of an enolate anion must be done using either a primary,primary allylic or primary benzylic species because the substitution follows an ___ mechanistic pathway.

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Which of these compounds would exist primarily in an enol form?


A) Which of these compounds would exist primarily in an enol form? A) B) C) D) E)
B) Which of these compounds would exist primarily in an enol form? A) B) C) D) E)
C) Which of these compounds would exist primarily in an enol form? A) B) C) D) E)
D) Which of these compounds would exist primarily in an enol form? A) B) C) D) E)
E) Which of these compounds would exist primarily in an enol form? A) B) C) D) E)

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Explain why the following tautomer equilibrium lies far to the right. Explain why the following tautomer equilibrium lies far to the right.

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Conjugated system wi...

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Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity: Considering only the highlighted hydrogens,list the following compounds in order of decreasing acidity: A) I,II,III,IV,V B) III,V,IV,I,II C) III,I,II,V,IV D) IV,V,II,I,III E) V,IV,III,II,I


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

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What would be the major product of the following reaction? What would be the major product of the following reaction? A) I B) II C) III D) IV E) V


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

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The conversion of The conversion of is accomplished by the use of which oxidizing agent? A) Ag(NH<sub>3</sub>) <sub>2</sub><sup>+</sup> B) O<sub>3</sub> C) NaOI (I<sub>2</sub> in NaOH) D) E) Cu<sup>2</sup><sup>+</sup> is accomplished by the use of which oxidizing agent?


A) Ag(NH3) 2+
B) O3
C) NaOI (I2 in NaOH)
D) The conversion of is accomplished by the use of which oxidizing agent? A) Ag(NH<sub>3</sub>) <sub>2</sub><sup>+</sup> B) O<sub>3</sub> C) NaOI (I<sub>2</sub> in NaOH) D) E) Cu<sup>2</sup><sup>+</sup>
E) Cu2+

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A compound,C5H10O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these?


A) A compound,C<sub>5</sub>H<sub>10</sub>O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these? A) B) C) CH<sub>2</sub>=CHCH<sub>2</sub>CHOHCH<sub>3</sub> D) E)
B) A compound,C<sub>5</sub>H<sub>10</sub>O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these? A) B) C) CH<sub>2</sub>=CHCH<sub>2</sub>CHOHCH<sub>3</sub> D) E)
C) CH2=CHCH2CHOHCH3
D) A compound,C<sub>5</sub>H<sub>10</sub>O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these? A) B) C) CH<sub>2</sub>=CHCH<sub>2</sub>CHOHCH<sub>3</sub> D) E)
E) A compound,C<sub>5</sub>H<sub>10</sub>O,reacts with phenylhydrazine and gives a positive iodoform test.The compound could be which of these? A) B) C) CH<sub>2</sub>=CHCH<sub>2</sub>CHOHCH<sub>3</sub> D) E)

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What would be the major product of the following reaction sequence? What would be the major product of the following reaction sequence? A) I B) II C) III D) IV E) V


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

Correct Answer

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What would be the major product of the following reaction sequence? What would be the major product of the following reaction sequence? A) I B) II C) III D) IV E) V


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

Correct Answer

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What would be the major product of the following reaction? What would be the major product of the following reaction? A) I B) II C) III D) IV E) V


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

Correct Answer

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


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

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What would be the major product of the following reaction? What would be the major product of the following reaction? A) I B) II C) III D) IV E) V


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

Correct Answer

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What would be the major product of the following reaction? What would be the major product of the following reaction? A) I B) II C) III D) IV E) V


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

Correct Answer

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What would be the major product of the following reaction sequence? What would be the major product of the following reaction sequence? A) I B) II C) III D) IV E) V


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

Correct Answer

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Which would be formed when 2-methylpropanal is dissolved in D2O containing NaOD?


A) Which would be formed when 2-methylpropanal is dissolved in D<sub>2</sub>O containing NaOD? A) B) C) D) E)
B) Which would be formed when 2-methylpropanal is dissolved in D<sub>2</sub>O containing NaOD? A) B) C) D) E)
C) Which would be formed when 2-methylpropanal is dissolved in D<sub>2</sub>O containing NaOD? A) B) C) D) E)
D) Which would be formed when 2-methylpropanal is dissolved in D<sub>2</sub>O containing NaOD? A) B) C) D) E)
E) Which would be formed when 2-methylpropanal is dissolved in D<sub>2</sub>O containing NaOD? A) B) C) D) E)

Correct Answer

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The pKa for protons on the carbon between two carbonyls is about 9-11.This greater acidity (as compared to single carbonyl systems)can be accounted for by ___.

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resonance delocaliza...

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When ethyl acetoacetate is treated with one equivalent of ethoxide ion followed by one equivalent of 1,2-dibromoethane compound,X is produced.Treatment of X with a second equivalent of ethoxide,produces Y.Further treatment of this product to conditions of saponification,acidification and heating produced a product,Z,that gives the following spectral data: 1H NMR: 0.88 δ\delta multiplet 13C NMR: Broad Band Decoupled: 10.40,21.17,29.84, 208.30 δ\delta 1.00 δ\delta multiplet DEPT 90: 21.17 δ\delta 1.96 δ\delta multiplet DEPT 135: positive signals at 21.17,29.84 δ\delta 2.24 δ\delta singlet negative signals at 10.40 δ\delta What is a reasonable structure for Z?

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Which of the following would not undergo racemization in base?


A) (S) -2-phenylbutanal
B) (S) -3-phenylbutanal
C) (S) -3-phenyl-2-butanone
D) (S) -3-methyl-2-phenylbutanal
E) All of these choices will undergo racemization in base.

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