6891 Organic Chemistry Practice Problems

Determine if the following alkene derivatives are E or Z.

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Do all seven atoms in a molecule of 1,2-propadiene exist in a single plane?

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How many atoms in the following cumulene are coplanar?

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How many atoms of the 7 atoms in the following cumulene are coplanar?

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How many atoms of the 10 atoms in the following cumulene are coplanar?

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Use VSEPR theory to deduce the hybridization state of the negatively charged carbon in the following cumulene derived carbanion. In which orbital does the electron pair reside in? What is its geometry?

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List the type and quantity of the orbitals for each of the three hybridization states of carbon. 

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A hydrocarbon with molecular formula C13H20 is chiral and has a structure such that one of its five sp3 hybridized carbon atoms is attached to four different acyclic substituents with formula C3H5. What is the structure of the hydrocarbon?

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A molecule with MF C4H9BrO contains a tertiary alcohol and a primary bromide. What is the structure? 

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A hydrocarbon has a molecular formula C6H12. It has no rings and is chiral. Provide a structure for the hydrocarbon (either stereoisomer is acceptable).

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Of the possible alkyl halides with molecular formula C5H5I, how many contain a 4-membered ring?

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What kind of orbital does the lone pair in a carbene rest in?

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What kind of orbital does the positive charge in a methyl cation rest in?

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Give the two other reasonable resonance structures for the molecule below, showing all lone pairs and formal charges. 

(a) Circle the MAJOR resonance structure. 

(b) Briefly explain why you circled the structure you did for the major resonance structure.

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What is the IUPAC name for the molecule below?

a. 2-chloro-4-ethyl-1,5-dimethylcyclohexane 

b. 4-chloro-2-ethyl-1,5-dimethylcyclohexane 

c. 1-chloro-5-ethyl-2,4-dimethylcyclohexane 

d. 5-chloro-1-ethyl-2,4-dimethylcyclohexane

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Which bond is formed from the interaction of an sp3 hybridized orbital with an sp hybridized orbital?

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Write an acceptable IUPAC name for the compound below. Include 'cis' and trans' as part of the name when stereochemistry is illustrated. The IUPAC name is

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Provide a systematic name of the following compound:

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Draw the compound with the fewest carbons that fits the description.

an alkene and a tertiary alcohol

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Give the IUPAC name for the following alkane.

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Provide the correct IUPAC name for the below molecule. Be careful to include all dashes and commas in the correct locations.

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Spell out the full name of the compound.

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Spell out the full name of the compound.

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Spell out the full name of the compound.

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Spell out the full name of the compound.

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