CHAPTER 8 - Practice Exercises (ORGANIC CHEM I )______DR. PAHLAVAN

1. Give IUPAC names for the following compounds.

2. Draw structures corresponding to the following names;

a) 4- Bromo-3,3-dimethyl-1-hexen-5-yne b) Ethynylcyclopentane

c) 2,5,5- Trimethyl-3-heptyne d) 3,6-Heptadien -1 – yne

e) 2,4- Octadiene - 6 – yne f) Diphenyethyne(diphenylacetylene)

g) 3-sec- butyl-1- heptyne h) Decyne

i) Trans-1,2-diethynylcyclohexene j) 1,3,5 - heptatriyne

3. Synthesis the following compounds using 1-pentyne as the only source of carbon along with any inorganic

reagents you need. More than one step may be needed.

a) 2-hexanoneb) 3,4-dichloroheptane

4. Predict the products of the following reactions;

5. Predict the products from the reaction of following compounds with the following reagents;

I) 1- pentyneII) 2-heptyneIII) cyclohexyne

a) 1 eq. HBrb) 1 eq. Br2c) H2/ Lindlar catalystd) Li in NH3

e) Excess Br2f) 2 eq. HClg) Excess H2, Pd/Ch) HgSO4, H2SO4/H2O

i) NaNH2 in NH3 / CH3CH2Br j) BH3, THF and H2O2, OH –

  1. Compound A (C9H12) on catalytic hydrogenation over a Pd/C, absorbs 3 equivalents of H2 to give compound B (C9H18). Ozonolysis of compound A gavea ketone, that was identified as cyclohexanone. Compound A also reacts withNaNH2 /NH3 followed by addition of CH3Br gave compound C(C10H14). What are the structures of A, B, and C.
  1. Identify structures for compounds A, B, C, D, E and F.
  1. How would you carry out the following reactions (identify reagents).

  1. How would you carry out each of the following synthesis. Each reaction required more than one step.

Using acetylene and any alkyl halides as starting materials synthesis the folloewing compounds.

  1. Show reagents and experimental conditions required to bring about the following transformations.

Identify 1 –11.

  1. Alkene vs. alkyne selectivity- Provide the product for each reaction. Pay close attention to

regioselectivity, stereoselectivity, and chemoselectivity. This exercise is for one functional group vs.

another functional group.

1