Organic Chemistry Worksheets

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1 Highlight the single longest, continuous carbon-carbon chain. Note the alkyl branches that are connected to the root chain. Count the carbons in the root chain, starting from the end closest to the alkyl branches. 1. All alkanes have saturated bonds. Describe what is meant be this. 2. What is the formula for each of the following. a. ethane b. butane c. heptane d. decane Name each of the following. i) ii) CH 3 CH 2 CH 2 CH CH 2 CH 3 CH 3 CH 3 CH 3 CH 3 CH CH CH 3 iii) iv) CH CH 3 CH 3 3 CH 3 CH CH CH 2 CH CH 3 C CH 2 CH CH 2 CH 3 3 CH 2 CH 2 CH 3 Write structural formulas for each of the following. i) 3-ethylhexane ii) 2,4-dimethylheptane iii) 3,4-dimethyl-3-methylhexane CH 3

2 Separating Mixtures of Organic Compounds Crude oil is a mixture of many different compounds Crude oil cannot be used until its components are separated Physical Methods of Separation Fractional distillation is a physical method It separates a mixture on the basis of boiling points (a physical property) Oil refineries use a tower to do this Solvent extraction is used to purify the residue of fractional distillation The residue contains hydrocarbons with a high molar mass Solvents are mixed with this residue to dissolve impurities Separation is based on the physical property of like dissolves like

3 Chemical Refining The fractions can also be chemically refined to make them more useful Two processes: Cracking and Reforming Cracking Reforming Assignment Page 582 Questions 1-8 (you may have to read Section 14.4 in your textbook) Substitution Reactions 1. Fill in the following table Organic Reactant Reagent that Supplies Substituting Atom Atom or Group That is Replaced Product Alkane Cl 2 or Br 2 H Alkyl halide UV light Other Reagents or Conditions Needed benzene H alcohol Alkyl halide

4 2. For the following substitution reactions write a balanced equation using condensed structures for any organic reactant or product. Indicate any catalysts or special conditions required. If more than one organic product can form draw structures and name both. Ethane reacts with bromine in the presence of UV light Propan-2-ol reacts with hydrogen chloride 1-bromobutane reacts with sodium hydroxide Methylbenzene reacts with chlorine in the presence of a catalyst Butan-1-ol reacts with hydrogen iodide 2-chlorobutane reacts with sodium hydroxide Butane reacts with chlorine in the presence of UV light Review Theory 1. The number of carbon compounds far exceeds the number of all other types of chemical compounds. This is largely due to the ability of carbon to form different types of bonds. Discuss these types of bonds and provide an example of each.

5 2. The arrangement of atoms, within certain groups of molecules, that are believed to be responsible for the properties of these compounds are called. 3. Separating complex mixtures into purified components is called. 4. Fractional distillation is the separation of petroleum products by. 5. The number of carbon atoms in a compound has a large impact on its physical state at room temperature. The range for gases is to, for liquids is to, for solids is to 6. Crude oil has many hydrocarbons present, some of which are very large. To break down these large molecules to useable size is called. There are two types called and. 7. The opposite to cracking is called. 8. For each group we have studied, draw the complete structural diagram and provide the general formula where indicated. The functional groups we have studied are as follows: 9. a) Alkanes: b) Alkenes: c) Alkynes: general formula; general formula: general formula: d) Aromatics: e) Halides: f) Alcohols: g) Carboxylic acids:

6 10. Many organic halides are carcinogenic. From your readings, list two. and. 11. Which of the alcohols is the most important in industrial applications?. 12. Where are carboxylic acids found in nature?. 13. List the groups of compounds that can undergo the following types of reactions. 14. Substitution: and 15. Addition: and 16. Combustion: 17. Elimination: Draw the organic compounds for each of the following reactions and identify the type of reaction butene + hydrogen --> butane a) 2- propanol acid propene " "# + water 19. propane + bromine light 2- bromopropane + hydrogen bromide " "#

7 20. propyne + excess hydrogen --> propane a) 1- butanol acid 1- butene " "# + water 21. benzene + chlorine light chlorobenzene +hydrogen chloride " "# pentene + hydrogen chloride --> 2- chloropentane Name the following structures. 23. CH 3 -(CH 2 ) 3 -CH 3 CH3-CH2-CH2-CH2-CH-CH3 CH2 CH2 24. CH3 CH3 -CH =C-CH2-CH3 CH2 25. CH3

8 CH = C-CH 2-CH-CH3 26. CH3 CH3-27. CH3- CH3- -CH2-CH3 28. CH3-CH =CH- OH CH3-CH2-CHCl-CH3 F H C=C 31. H F OH 32. OH CH3-CH2-C 33. O Br Br H - C - C - H 34. Br Br OH CH3 -C 35. O or

9 OH CH3-CH-CH-CH2-CH3 36. OH CH3-CH2-CH2-CH2-CH2-CH Draw and name the 5, non- cyclic, isomers of hexane

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