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Consider the information given below and identify the structure of the unknown compound A, with a molecular formula of C8H14. Compound A reacts with Br2/CCl4. Upon reaction of A with excess H2/Ni 1-ethyl-2-methylcyclopentane is produced. Subjecting A to ozonolysis, the product shown below is produced as the major organic product. Draw the correct structure of compound A, and provide a brief and clear explanation relating the data provide with the structure selected. Consider the information given below and identify the structure of the unknown compound A, with a molecular formula of C<sub>8</sub>H<sub>14</sub>. Compound A reacts with Br<sub>2</sub>/CCl<sub>4</sub>. Upon reaction of A with excess H<sub>2</sub>/Ni 1-ethyl-2-methylcyclopentane is produced. Subjecting A to ozonolysis, the product shown below is produced as the major organic product. Draw the correct structure of compound A, and provide a brief and clear explanation relating the data provide with the structure selected.

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A must be 3-ethyl-4-...

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What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?


A) Markovnikov addition of H2O, promoting skeletal rearrangement
B) Markovnikov addition of H2O, preventing skeletal rearrangement
C) anti-Markovnikov addition of H2O, promoting skeletal rearrangement
D) anti-Markovnikov addition of H2O, preventing skeletal rearrangement
E) anti-Markovnikov addition of H2O, syn-hydroxylation

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The regioselectivity and stereospecificity in the oxymercuration of an alkene is best described as:


A) Markovnikov orientation with syn-addition
B) Markovnikov orientation with anti-addition
C) anti-Markovnikov orientation with syn-addition
D) anti-Markovnikov orientation with anti-addition
E) Markovnikov orientation with both syn- and anti-addition

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The expected product(s) resulting from addition of Br2 to (E) -3-hexene would be:


A) a meso dibromide.
B) a mixture of optically active enantiomeric dibromides.
C) a mixture of optically inactive enantiomeric dibromides.
D) (Z) -3,4-dibromo-3-hexene.
E) (E) -3,4-dibromo-3-hexene.

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What is the expected major product for the following reaction? What is the expected major product for the following reaction? A) B) C) D) E)


A) What is the expected major product for the following reaction? A) B) C) D) E)
B) What is the expected major product for the following reaction? A) B) C) D) E)
C) What is the expected major product for the following reaction? A) B) C) D) E)
D) What is the expected major product for the following reaction? A) B) C) D) E)
E) What is the expected major product for the following reaction? A) B) C) D) E)

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For the following reaction draw out the expected major organic product(s). Include regiochemical and/or stereochemical details as relevant, and provide a short justification for the product(s) drawn. For the following reaction draw out the expected major organic product(s). Include regiochemical and/or stereochemical details as relevant, and provide a short justification for the product(s) drawn.

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blured image The reaction takes place with...

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In conducting a catalytic hydrogenation of an alkene, which catalyst listed is most likely soluble in the reaction medium?


A) Ni
B) Pt
C) Pd
D) Wilkinson's catalyst
E) All of the above are soluble

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Which of the following alkene addition reactions occur(s) specifically in an anti fashion?


A) hydroboration-oxidation
B) addition of Br2
C) addition of H2
D) addition of H2O in dilute acid
E) both A and B

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Which of the following alkenes will yield a meso dihalide when reacted with Br2/CCl4 at room temperature?


A) Which of the following alkenes will yield a meso dihalide when reacted with Br<sub>2</sub>/CCl<sub>4</sub> at room temperature? A) B) C) D) E) Both B and D
B) Which of the following alkenes will yield a meso dihalide when reacted with Br<sub>2</sub>/CCl<sub>4</sub> at room temperature? A) B) C) D) E) Both B and D
C) Which of the following alkenes will yield a meso dihalide when reacted with Br<sub>2</sub>/CCl<sub>4</sub> at room temperature? A) B) C) D) E) Both B and D
D) Which of the following alkenes will yield a meso dihalide when reacted with Br<sub>2</sub>/CCl<sub>4</sub> at room temperature? A) B) C) D) E) Both B and D
E) Both B and D

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What is the expected major product of the following reaction sequence? What is the expected 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

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What is the expected major product for the following reaction? What is the expected major product for the following reaction? A) B) C) D) E)


A) What is the expected major product for the following reaction? A) B) C) D) E)
B) What is the expected major product for the following reaction? A) B) C) D) E)
C) What is the expected major product for the following reaction? A) B) C) D) E)
D) What is the expected major product for the following reaction? A) B) C) D) E)
E) What is the expected major product for the following reaction? A) B) C) D) E)

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Identify the expected major organic product resulting from the following reaction sequence. Identify the expected major organic product resulting from 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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Provide the expected major organic product from the reaction shown below. Provide a brief explanation of any regioselectivity the reaction is expected to produce. Provide the expected major organic product from the reaction shown below. Provide a brief explanation of any regioselectivity the reaction is expected to produce.

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blured image The alcohol will be found at the tertia...

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Provide the expected major organic product of the reaction sequence shown. Provide the expected major organic product of the reaction sequence shown. A) I and II B) IV and V C) I only D) II only E) III only


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

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What is the expected major product upon reaction of 1-pentene with Cl2?


A) 1-chloropentane
B) 2-chloropentane
C) 1,1-dichloropentane
D) 2,2-dichloropentane
E) 1,2-dichloropentane

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The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as:


A) Markovnikov orientation with syn-addition
B) Markovnikov orientation with anti-addition
C) Anti-Markovnikov orientation with syn-addition
D) Anti-Markovnikov orientation with anti-addition
E) Markovnikov orientation with both syn- and anti-addition

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What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?


A) 1-chloro-2-methylbutane
B) 1-chloro-3-methylbutane
C) 2-chloro-2-methylbutane
D) 2-chloro-3-methylbutane
E) 1-chloropentane

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For the following transformation below, provide a detailed step-wise mechanism showing the electron flow using the curved arrow formalism. For the following transformation below, provide a detailed step-wise mechanism showing the electron flow using the curved arrow formalism.

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Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?


A) 2,3-dibromo-2-methylpentane
B) 2,2-dibromo-3-methylpentane
C) 3,3-dibromo-2-methylpentane
D) 2-bromo-2-methylpentane
E) 3-bromo-2-methylpentane

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Which of the following will yield 2-methylpentane upon catalytic hydrogenation?


A) 2-methyl-1-pentene2
B) 2-methyl-2-pentene
C) 4-methyl-2-pentene
D) 4-methyl-1-pentene
E) All of the above

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