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Exam 7: Structure and Synthesis of Alkenes; Elimination

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Question 31

Multiple Choice

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How many elements of unsaturation do molecules with a molecular formula of C₆H₆Cl₆ have?

A) 0
B) 1
C) 2
D) 3
E) 4

F) D) and E)
G) B) and D)

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Question 32

Multiple Choice

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Using Zaitsev's rule, choose the most stable alkene among the following.

A) 1-methylcyclohexene
B) 3-methylcyclohexene
C) 4-methylcyclohexene
D) They are all of equal stability according to Zaitsev's rule.

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

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Question 33

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Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Draw all likely alkene products in the following reaction and circle the product you expect to predominate.

Draw an acceptable structure for 4-ethylhept-1-ene.

Which of the following alkenes has the largest molar heat of hydrogenation (ie, releases the most heat upon hydrogenation) ?

Provide a model that shows why the less stable Z isomer is formed in this reaction shown.

Which of the following alkenes can show geometric isomerism: 2,3-dichloro-2-pentene, 4-chloro-3-ethyl-3-hexene, 3-chloro-2-methyl-2-butene, and 3-chloro-2-methyl-1-butene?

Propose a detailed, step-by-step mechanism for the reaction pathway shown below.

Which of the following alkenes is the major product when 2-bromo-2-methylpentane is treated with potassium tert-butoxide in tert-butanol?

Provide a synthesis to convert but-1-ene to buta-1,3-diene.

Draw an acceptable structure for (Z)-2-chloro-4-ethylhex-2-ene.

Provide the major organic product in the reaction shown below.

Provide the name of the major alkene product that results when (2S,3R)-2-bromo-3-methylpentane is treated with sodium methoxide in methanol.

Draw a mechanism for the reaction shown below.

Draw an acceptable structure for 4-phenylbut-1-ene.

Provide the proper IUPAC name for the alkene shown below.

Which base, ammonia (NH₃) or triethylamine [(CH₃CH₂)₃N], would be a better choice for use in converting 1-chlorohexane to hex-1-ene? Explain briefly.

Provide a series of steps through which 2-methylbutane is converted into 2-methylbut-1-ene.

How many elements of unsaturation are implied by the molecular formula