Chem 2411 – Organic Chemistry I chapter 3: Additional Problems

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CHEM 2411 – Organic Chemistry I

Chapter 3: Additional Problems

  1. (McMurry 3.12) Give IUPAC names for the following compounds:

a. The 3 isomers of C5H12. b.

n-pentane 3,4-dimethylhexane

isopentane (2-methylbutane)

neopentane (2,2-dimethylpropane)

c. d.

2,4-dimethylpentane 2,2,5-trimethylheptane

  1. (McMurry 3.13) Draw structures corresponding to the following IUPAC name:

a. 3,4-Dimethylnonane b. 3-Ethyl-4,4-dimethylheptane

c. 2,2-Dimethyl-4-propyloctane d. 2,2,4-Trimethylpentane

  1. (McMurray 3.16) Give IUPAC names for the following cycloalkanes:

a. b.

1,4-dimethylcyclohexane 1-methyl-3-propylcyclopentane
c. d.

3-cyclobutylpentane 1-bromo-4-ethylcyclodecane
e. f.

1-isopropyl-2-methylcyclohexan 4-bromo-1-tert-butyl-2-methylcycloheptane

  1. (McMurray 3.17) 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

  1. (McMurry 3.18) Name the following substances, specifying each as cis or trans:

a. b.

Trans-1-chloro-4-methylcyclohexane cis-1-ethyl-3-methylcycloheptane

  1. (McMurry 3.19) Draw the structures of the following molecules:

    1. trans-1-Bromo-3-methylcyclohexane

    1. cis-1,2-Dimethylcyclopentane

    1. trans-1-tert-Butyl-2-ethylcyclohexane

  1. (McMurry 3.29) Draw as many compounds as you can that fit the following descriptions:

    1. Alcohols with formula C4H10O

    1. Amines with formula C5H13N

    1. Ketones with formula C5H10O

    1. Aldehydes with formula C5H10O

    1. Esters with formula C4H8O2

    1. Ethers with formula C4H10O

  1. (McMurry 3.34) Draw structures for the following:

    1. 2-Methylheptane

    1. 4-Ethyl-2,2-dimethylhexane

    1. 4-Ethyl-3,4-dimethyloctane

    1. 2,4,4-Trimethylheptane

    1. 3,3-Diethyl-2,5-dimethylnonane

    1. 4-Isopropyl-3-methylheptane

  1. (McMurry 3.40) Give IUPAC names for the following compounds:

a. b.

2-methylpentane 2,2-dimethylbutane
c. d.

2,3,3-trimethylhexane 5-ethyl-2-methylheptane
e. f.

3,3,5-trimethyloctane 2,2,3,3-tetramethylhexane


  1. (McMurry 3.42) Explain why each of the following names is incorrect:

The best way to answer these questions is to draw the structure as named, to see why it is incorrect

    1. 2,2-Dimethyl-6-ethylheptane


    1. 4-Ethyl-5,5-dimethylpentane


    1. 3-Ethyl-4,4-dimethylhexane


    1. 5,5,6-Trimethyloctane


    1. 2-Isopropyl-4-methylheptane


    1. cis-1,5-Dimethylcyclohexane


  1. (McMurry 3.44) Give IUPAC names for the following compounds:

a. methylcycloheptane

b. cis-1,3-dimethylcyclopentane

c. trans-1,2-dimethylcyclohexane

d. trans-1-isopropyl-2-methylcyclobutane

e. 1,1,4-trimethylcyclohexane

  1. (McMurry 4.27) Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane. Which conformation would you expect to be more stable? Label the anti and gauche conformations of 1,2-dibromoethane.

  1. (McMurry 4.31) Draw the most stable conformation of 1,4-dichlorobutane, using wedges and dashes to represent bonds coming out of the paper and going behind the paper, respectively.

  1. (McMurry 4.32) Draw a chair cyclohexane ring and label all positions as axial or equatorial.

  1. (McMurry 4.33) Why is a 1,3-cis disubstituted cyclohexane more stable than its trans isomer?

  1. (McMurry 4.35) Which is more stable, a 1,4-trans disubstituted cyclohexane or its cis isomer?

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