Chemistry 22002 Hydrocarbon Derivatives1

Lab Activity 10: Hydrocarbon Derivatives

Introduction

Hydrocarbon derivatives differ from pure hydrocarbons in terms of composition and properties. In this activity, you will use a molecular models kit to build models of hydrocarbon derivatives and relate their structures to their physical and chemical properties.

Textbook Readings

MHR Chemistry

  • Section 10.1: Functional Groups, pages 377-379, pages 381-382
  • Section 10.2: Single Bonded Functional Groups, pages 389-391
  • Section 10.3: Functional Groups with C=O Bond, page 407

Problem

How are the properties of hydrocarbon derivatives related to their function groups?

Pre-Lab Assignment

Complete the prelab component of the table as homeworkbefore you build the models in the lab during class time. You are required to provide the missing name, molecular formula, or structural formula for each row in the table. For each substance in a row, complete an intermolecular force analysis (i.e. count electrons per molecule, describe the shape, state polarity, indicate hydrogen bonding potential, list intermolecular forces present).

Materials

per pair of students:

  • one molecular model kit
Safety
  1. Be careful when inserting springs into the balls. Twist the spring into and out of the hole in the ball to prevent damage to the spring.
  2. Wear eye protection because the springs sometimes come loose and become flying projectiles.
Procedure

Molecular Models Kit Method

  1. Construct a model for each compound and one of its isomers.
  2. Photograph the models. Be sure to make labels for your models using a marker and paper.

When using a molecular model kit, use this key or the one provided in the kit:

Chemistry 22002 Hydrocarbon Derivatives1

  • carbon: black balls (4 hole)
  • hydrogen: yellow or white balls (1 hole)
  • oxygen: red (2 hole)
  • halogen: green (1 hole)
  • nitrogen: blue (4 or 5 hole)
  • single bond: wooden stick
  • double or triple bonds: springs

Chemistry 22002 Hydrocarbon Derivatives1

ACD Chemsketch/3D Viewer Software Method

  1. To generate a condensed diagram in ChemSketch, click in the whiteboard to add the first carbon. Then position your mouse over this carbon and click again to add a second carbon. Continue adding carbon atoms to form a chain or a branched chain.
  2. To add a non-carbon element like O, position your mouse so the carbon you want to add onto is highlighted in a rectangle. Drag away from this carbon (don't click on it) and then release the mouse button.
  3. To convert a single bond to a double or triple bond, click once the bond to make a double bond and twice to make a triple bond.
  4. To convert the condensed diagram to a 3D structure,click on ACD/Labs in the menu bar, and then select 3D viewer. Alternatively, you can use the 3-D viewer icon. Once you have loaded the viewer, you can switch from ChemSketch to 3D view using the tabs at the bottom left of your screen.
  5. To get the correct shape and view of your molecule, select the "Balls and Sticks" view from the toolbar, and select 3D Optimization from the toolbar.
  6. In the 3D Viewer screen, print each molecule to a .pdf file. If the printer is not set up to print to .pdf, change the printer by clicking on File > Printer Setup and selecting Adobe PDF. Save each model by its number above. E.g. 1a.pdf.
  7. If you are unable to print the images as pdf files, then click on File  Save Asand enter a file name for the image, e.g. 1a.s3d
  8. Build the structure of the isomer and repeat steps 6 or 7.
  9. If you saved your files as .s3d files, then zip them into one file called images.zip using WinZip.
  10. If you created pdf files, then try to merge these files by opening all the files, clicking on the page tab on the left or each one, and dragging each page into one. Save this file as images.pdf.

Chemistry 22002 Structures and Properties of Hydrocarbon Derivatives1

Name: ______Site: ______

Pre-Lab Table

Molecular Formula / Structural Formulaand Name / Intermolecular Force Analysis / Structural Formula and Name of an Isomer / Intermolecular Force Analysis
1.a
C2H2Cl2 / 1.b
Name: / Name:
2.a
C2H5OH / 2.b
Name: / Name: methoxymethane
3.a / 3.b
Name: propanal / Name:
4.a / 4.b
Name: propanoic acid / Name: methyl ethanoate

Chemistry 22002 Structures and Properties of Hydrocarbon Derivatives1

Name: ______Site: ______

Analysis:
  1. Write a structural formula equation to illustrate the addition polymerization of C2H2Cl2.
  1. The boiling points of the isomers of C2H6O(2a and 2b above) are 78˚Cand -22˚C.

Match each isomer with a boiling point and provide an explanation to support your choice. In your explanation, refer to similarities and differences in the intermolecular forces of these substances.

3.Ethanol and propanone (commonly known as acetone) are often used as solvents for polar or nonpolar substances.

Which substance should be more soluble in water? Explain your choice in terms of differences in intermolecular forces.

4.Write a complete balanced structural formula equation for the formation of methyl ethanoate from methanol and ethanoic acid.

5. Match the structure on the left with the name of an isomer on the right

Match Letter / Structure / Isomer
______/ / a) pentanoic acid
______/ / b) 2-chloropropane
______/ / c) methoxypropane
______/ / d) 1-propanol
______/ / e) pentanal