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When the two constitutional isomers, 3,3-dimethyl-1-butene and 2,3-dimethyl-2-butene, are reacted with HCl the same major product is formed. Provide an explanation for the observation.

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blured image_TB4454_00 For the unsymmetrical 3,3-dim...

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Give the expected product(s) resulting from addition of Br2 to (E) -3-hexene.


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

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Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme: Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme:

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blured image_TB4454_00...

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What is the expected major product for the following reaction sequence? What is the expected major product for the following reaction sequence? A) I B) II C) III D) IV E) V What is the expected major product for 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 the following will yield 2-methylpentane upon catalytic hydrogenation?


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

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Give the best description for the regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene.


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 are the expected major products from the reaction sequence shown below? What are the expected major products from the reaction sequence shown below? A) I B) II C) III D) IV E) V What are the expected major products from the reaction sequence shown below? A) I B) II C) III D) IV E) V


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

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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 statements is most correct regarding the products expected from the halogenation reaction shown below? Which of the statements is most correct regarding the products expected from the halogenation reaction shown below? A) Equal amounts of I and II are produced. B) Equal amounts of III and IV are produced. C) Equal amounts of I and IV are produced. D) Equal amounts of II and III are produced. E) Equal amounts of I and III are produced. Which of the statements is most correct regarding the products expected from the halogenation reaction shown below? A) Equal amounts of I and II are produced. B) Equal amounts of III and IV are produced. C) Equal amounts of I and IV are produced. D) Equal amounts of II and III are produced. E) Equal amounts of I and III are produced.


A) Equal amounts of I and II are produced.
B) Equal amounts of III and IV are produced.
C) Equal amounts of I and IV are produced.
D) Equal amounts of II and III are produced.
E) Equal amounts of I and III are produced.

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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_TB4454_00 The reaction takes ...

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In an addition reaction to an alkene, the π bond is ______.


A) a nucleophile
B) an electrophile
C) a leaving group
D) A and B
E) B and C

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Which of the molecules below arises from the anti-Markovnikov hydrohalogenation with HBr of the alkene shown? Which of the molecules below arises from the anti-Markovnikov hydrohalogenation with HBr of the alkene shown? A) I B) II C) III D) IV E) V Which of the molecules below arises from the anti-Markovnikov hydrohalogenation with HBr of the alkene shown? A) I B) II C) III D) IV E) V


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

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Identify the expected first intermediate formed during a halohydrin reaction.


A) a halonium ion.
B) the most stable carbocation with OH on the adjacent carbon.
C) the most stable carbocation with X on the adjacent carbon.
D) a cyclic oxonium ion.
E) the most stable carbanion.

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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 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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For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship. For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship. A) I and II; enantiomers B) III and IV; enantiomers C) I and II; diastereomers D) II and III; diastereomers E) III and IV; diastereomers For the following reaction sequence, identify the expected major organic products and provide their stereochemical relationship. A) I and II; enantiomers B) III and IV; enantiomers C) I and II; diastereomers D) II and III; diastereomers E) III and IV; diastereomers


A) I and II; enantiomers
B) III and IV; enantiomers
C) I and II; diastereomers
D) II and III; diastereomers
E) III and IV; diastereomers

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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 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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For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry. For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

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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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For the following dihydroxylation reaction which of the following statements is correct regarding the expected products? For the following dihydroxylation reaction which of the following statements is correct regarding the expected products? A) Equal amounts of I and II produced B) Equal amounts of III and IV produced C) Equal amounts of I and IV produced D) Equal amounts of II and III produced E) Equal amounts of I and III produced For the following dihydroxylation reaction which of the following statements is correct regarding the expected products? A) Equal amounts of I and II produced B) Equal amounts of III and IV produced C) Equal amounts of I and IV produced D) Equal amounts of II and III produced E) Equal amounts of I and III produced


A) Equal amounts of I and II produced
B) Equal amounts of III and IV produced
C) Equal amounts of I and IV produced
D) Equal amounts of II and III produced
E) Equal amounts of I and III produced

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The alkene precursor to ethanol is __________.

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