Quiz 3 (Chapters 4) Organic Chemistry

Give IUPAC names for the following cycloalkanes:

a) 1,4-dimethylcyclohexane

b) 1-methyl-3-propylcyclopentane

c) 3-cyclobutylpentane

d) 1-bromo-4-ethylcyclodecane

e) 1-isopropyl-2-methylcyclohexane

f) 4-bromo-1-tert-butyl-2-methylcycloheptane

Draw structures corresponding to the following IUPAC names:

(a) 1,1-Dimethylcyclooctane

(b) 3-Cyclobutylhexane

(c) 1,2-Dichlorocyclopentane

(d) 1,3-Dibromo-5-methylcyclohexane

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Name the following substances, including the cis- or trans- prefix:

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Draw the structures of the following molecules:

(a) trans-1-Bromo-3-methylcyclohexane

(b) cis-1,2-Dimethylcyclobutane

(c) trans-1-tert-Butyl-2-ethylcyclohexane

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Draw two different chair conformations of cyclohexanol (hydroxycyclohexane), showing all hydrogen atoms. Identify each position as axial or equatorial.

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Draw two different chair conformations of trans-1,4-dimethylcyclohexane, and label all positions as axial or equatorial.

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Identify each of the colored positions—red, blue, and green—as axial or equatorial. Then carry out a ring-flip, and show the new positions occupied by each color.

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Draw the more stable chair conformation of the following molecules, and estimate the amount of strain in each:

(a) trans-1-Chloro-3-methylcyclohexane

(b) cis-1-Ethyl-2-methylcyclohexane

(c) cis-1-Bromo-4-ethylcyclohexane

(d) cis-1-tert-Butyl-4-ethylcyclohexane

Identify each substituent in the following compound as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (green = Cl):

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Name the following cycloalkanes:

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Name the following compound, identify each substituent as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (green = Cl):

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A trisubstituted cyclohexane with three substituents—red, green, and blue—undergoes a ring-flip to its alternate chair conformation. Identify each substituent as axial or equatorial, and show the positions occupied by the three substituents in the ring-flipped form.

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The following cyclohexane derivative has three substituents—red, green, and blue. Identify each substituent as axial or equatorial, and identify each pair of relationships (red–blue, red–green, and blue–green) as cis or trans.

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Draw a stereoisomer of trans-1,3-dimethylcyclobutane.

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Tell whether the following pairs of compounds are identical, constitutional isomers, stereoisomers, or unrelated.

(a) cis-1,3-Dibromocyclohexane and trans-1,4-dibromocyclohexane

(b) 2,3-Dimethylhexane and 2,3,3-trimethylpentane

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Identify each pair of relationships among the –OH groups in glucose (red–blue, red–green, red–black, blue–green, blue–black, green–black) as cis or trans.

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