CHEM 30B  Dr. R. Rinehart            Alcohol, etc. Workshop 

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1)  Visit Dave Woodcock’s sites  http://www.molecularmodels.ca/molecule/Alcohols.htm , http://www.molecularmodels.ca/molecule/Phenols.htm  and  http://www.molecularmodels.ca/molecule/Ethers.htm .
Scroll down the lists of compounds, pick a few from each class for viewing, and record your observations below.

HINT: Use the right-click pop-up menu to change the display as needed. I suggest changing every display on each page to "Sticks" before doing anything else. Then rotate for best view. UNchecking the “Display Hydrogens” option is a big help in drawing line structures. You MUST indicate heteroatoms [and attached H] using their symbols. 

2)  Using Netscape*, go to http://c4.cabrillo.edu/chem30b/exercises/exerhome.html .  In the list under “Chime exercises,”  select  Chapter 13. There are twelve exercises. Do Exercises 1, 2, 3, 4, 5A,C,E,F; 6A,C,E; 7, 10, 11, and 12 and answer the questions asked on this worksheet  [or if you’re doing this outside class, use the link to print your own worksheet]. * I also was able to get this to work with the MS IE version of Chime, but Netscape is still recommended.

HINT: Use the right-click pop-up menu to change the display as needed. In most cases, the “Sticks” display is most useful, and unchecking the “Display Hydrogens” option is a big help in drawing line structures. You MUST indicate heteroatoms [and attached H] using their symbols.

Read and answer each question carefully and thoroughly. Please do not crowd your answers. Use the scratch paper to work out each problem and write the final answer on this worksheet. Problems which have answers are identified by an asterisk. You should do these problems first, check your answers, and then do the rest.

1. Give the IUPAC name and draw the line formula for each of the following models.

2. Arrange the following series of molecules in order of increasing boiling point.

Set 2.1*    lowest ____ ____ ____ ____ ____ highest

Set 2.2     lowest ____ ____ ____ ____ ____ highest

3. Which of the following compounds are isomers of the depicted molecule? Write the letters corresponding to the models in the space provided.

4. Each of the following compounds could be an isomer of C₄H₁₀O, C₄H₈O or neither.
Decide in which category each compound belongs. Use the letters of the models.
HINT: use SODAR to help: for every ring or double bond, there will be 2 fewer H.

5. Draw the line structure of each product (indicated by "?") in the following reactions. If no reaction is likely to occur, write NR and explain briefly.

6. Draw the structure of the alcohol that could be used to prepare each of the following compounds.
 

7. Classify the following compounds as containing primary, secondary or tertiary alcohols. Use the letters of the models.

<we’re skipping 8 and 9>

10. Among the following set of 8 models, there are two pairs of compounds that relate to each other by an oxidation/reduction process. In each pair identify the one which is more oxidized and the one which is more reduced. Use the letters of the modeld

11. a. Draw the structure of each compound. Show how each molecule hydrogen bonds to water molecules.

b. Show how each molecule hydrogen bonds to other molecules of the same compound.

12. Match each compound with one or two statements below. Statements may be used more than once. Use the letters of the statements.

a. Compound with sulfhydryl group   
b. Product of oxidation of an alcohol
c. Compound with tertiary alcohol     
d. Product of thiol oxidation
e. An alcohol that can not be oxidized  
f. Compound with an ether
g. Pair of compounds that are structural isomers

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