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Chemical Drawing & Word Processing Exercise Dr. Gergens – San Diego Mesa College Purpose Computer literacy is fast emerging as a basic skill that will be as important to life in the twenty-first century as reading is now. The purpose of this exercise is to give students practical experience in computer literacy by developing some general computer word processing and chemical drawing skills needed for this course. In particular, students should be able to draw chemical struc tures— perhaps using a drawing program like ISIS Draw—import and edit images, and save and insert images from web based sources into their reports. In the process, you will be exposed to the use of chemical data base, (i.e., http://www.chemfinder.com, http://www.chemexper.com), to track down chemical data as well. Finally, students will be given the opportunity to learn the basics of scanning data and images, saving the scanned information to disk, and importing and word processing that information into their report. To assist you in learning to draw chemical structures, you will find a tutorial covering some simple basics for drawing chemical structure, and how to select, resize , and import chemical structure into a word document. Getting Started There are several chemical drawing programs available in the laboratory. Most drawing and word processing programs on the market generally have the same generic look and feel. If you are already accustom to using a drawing program, good for you. In this course, use what ever drawing and word processing programs you are most familiar and comfortable with in word processing your laboratory reports. One chemical drawing program commonly used by students in our chemistry department is ISIS Draw. Another program is Microsoft Word which most already use for general word processing. If you're new to ISIS Draw, you might be terrified. Once you review the tutorial and get going though you'll see you can create professionally great graphics simply by clicking on your screen. ISIS Draw has a complete set of tools and templates for creating many different kinds of drawings, but we will use it mainly to draw chemical structures. In general, students can access ISIS Draw from most computers on campus. Students can find access to computers in I-110, K-400, and on the fourth floor of the library to be most convenient. ISIS Draw, ChemSketch & Marvin Sketch are also available as a free download and their URL’s a listed under the Chemical Structure Drawing and Word Processsing Exercise under experiments at http://homework.sdmesa.edu/dgergens/chem231L/index.html . Exercise Welcome to ISIS Draw. To start in learning the basics, find a computer with ISIS Draw loaded and that has Internet access. Open ISIS Draw and either Netscape or Explorer. Access the ISIS draw tutorial link and click on it. The ISIS tutorial at http://homework.sdmesa.edu/dgergens/chem231L/ISIS/isis_tutorial_frame.html . These tutorials are QuickTime movies. QuickTime Movie Player should be installed on your computer. If it is not, link to the QuickTime movie page, download and install the movie player. I would suggest watching the tutorial first then mimic the same process using ISIS Draw. Some of you may be even cl ever enough to resize your viewing screen so both ISIS Draw and the browser windows are viewable at the same time. In this way, you would be able to watch the movie and following along using ISIS Draw at the same time. The tutorial will answer most of your questions regarding the use of the program. If you have additional questions and/or suggestions regarding the tutorial, you can e-mail at [email protected] . Download from the same web page the ISIS Draw Assignment. This is the ISIS Draw Assignment is the word document that will be word processed and turned in for grading. You can use any drawing program to draw (i.e., ChemSketch or Marvin Draw) but the tutorials demonstrate the use of ISIS Draw only. An important note on importing images. When importing or pasting an image from ISIS into a Microsoft Word document, select and copy the image in ISIS, then paste into Word by selecting <Insert>, <Paste Special>, and select <Enhanced Meta File>. This is very important to remember. "A picture is worth a thousand (by a thousand) words" PART A - Cleaning Up Hand Drawn Images In this exercise, you are being asked to redraw exact duplicates of these hand drawn chemical structures by using any chemical drawing program you are most familiar with. It is recommended you use ISIS Draw to redraw the structures but using other drawing programs to complete this assignment is acceptable as well. Word process each drawing or image into the table cells provided for your in this document. Watch the line-angle video http://homework.sdmesa.edu/dgergens/chem231L/ISIS/_line_angle.html to understand what is implied by the shown line-angle structures so your can determine correct molecular formulas as well. Redraw exact duplicates of chemical structures using a chemical drawing program. Then cut and paste each image into the box on the right of each hand drawn image. Resize each image so all eight structures can fit on this page. Finally, identify the functional group and correct molecular formula. An example, ethyl butanoate, an ester, is done for you. Hand Drawn Compound & Structure functional group and formula ethyl butanoate Re-Drawn Compound & Structure ethyl butanoate ester C6H12O2 O CH3CH2CH2 C OCH2CH3 N-ethylaniline N-ethylaniline 4-isopropyltoluene 4-isopropyltoluene 2-methylpropanoic acid 2-methylpropanoic acid polyethylene polyethylene 3-bromopropyne 3-bromopropyne adipoyl chloride adipoyl chloride PART B - Saving and Inserting Web Based Images In this exercise, you are being asked to use the internet as a resource of pre-drawn chemical structures. Often we will have to search for physical data (e.g., structure, mp, bp) on a compound using a data base. In our search, most data bases in general will give the structure of the compound as an image. Images can be save to disk to be inserted into a word document at a later ti me. This should save us time and effort in not having to re-draw each structure. Use any search engine to seach for images of the below compounds (i.e., http://www.chemfinder.com, http://www.chemexper.com, http://www.google.com/imghp ). Searching by molecular formula will give a much broader search result for the given compound. To do a molecular search, be sure that you total the number of atoms—and hydrogens—are added up correctly. Search by molecular formula first, then match the name to structure. To copy an image from the internet, place the cursor on the image, mouse cl ick and hold, select <Save Image As.> and save the image to disk. Find the saved image and insert it into the box on the left. When inserting a saved image into a Microsoft Word document, select <Insert>, <Picture>, <From file>, select the <file name>. If the image does not go into the desired cell in the table, you m ay have to copy the image then paste back into Word by selecting <Insert>, <Paste Special>, and select <Enhanced Meta File>. We would like the image to fit into the box at the left without having the box expanding larger than what it is currently. All eight structures need to be resized to fit on this page. The first one the ester, ethyl 2-bromo-2-methylpropionate, is done for you. Web Base Image functional group and formula Compound & Structure ethyl 2-bromo-2-methylpropionate ester C6H11BrO2 O (CH3)2C C OCH2CH3 Br 1-phenyl-2-propanone O CH2CCH3 3,7-dimethyl-6-octenal H O 3-methyl-1-butanol (CH3)2CHCH 2CH 2OH 2-aminotoluene NH2 CH3 3-methyl-3-buten-2-one O PART C - Editing a Chemical Structure In this exercise, you are being asked to draw and import the structure of Tylenol into the cell below. For caffeiene, you are being asked to search the internet for a pre-drawn chemical structure for caffeine. Once you are added each image to each table cell below, you will need to edit the image in Microsoft word. For example, cyclohexanone was imported using ChemFinder and it was also drawn in ISIS Draw. Then in Microsoft Word, the image was edited by using the drawing tools which are usually found at the bottom of the Microsoft Word application. From the tool box in MS Word an arrow was added to each image. cyclohexanone (Drawn by ISIS Draw) cyclohexanone (Imported from Chemfinder) O Draw the structure of Tylenol and import its image into the box on the left. Use the internet to obtain a pre-drawn image of caffeine and insert into the box at the right. Finally, edit both images by double clicking on both images while in MS Word and add an arrow and a star to each image. Compound & Structure Tylenol (Drawn by ISIS Draw) Compound & Structure caffeine (Imported from Chemfinder) PART D - Editing a Scanned Image (SKIP THIS SECTION) In this exercise, you will be asked to scan an FTIR spectrum of Nujol oil and save it to disk. Afterwards, you will asked to recall that image and insert it into a word document. Finally, you will be asked to edit the image in Microsoft Word. For example, the scanned spectrum of Nujol oil was imported and then edited by adding the labels C-H stretching and C-H bending, and a title was given. Have available a disk with this assignment document file on it. You will scan an image to this disk. In the laboratory there is a scanner. You will need to save the scanned image to the same disk that has this assignment document file. Obtain a sample FTIR spectrum of Nujol oil from your instructor. Scan the image of FTIR spectrum of Nujol oil followi ng the procedures "How to Scan" posted near the scanner. Name the scanned image file <Nujol.doc> and save the image and file to disk. Is the <Nujol.doc> image file on the same disk with the file for this assignment? If so, open the <Nujol.doc> and the file for this assignment. From the <Nujol.doc> document, select and copy the FTIR spectrum. Do a <Insert>, <Paste Special>, <Enhanced Meta File> to insert the FTIR spectrum for Nujol into box below for this assignment. Finally, edit the FTIR spectrum for Nujol by double clicking on the image and adding the labels C—H stretching and C—H bending, and by giving the spectrum a title. We would like the image to fit into the box below without having the box expanding large r than what it is currently. Your scanned image should remain on this page. PART E - Use of Chemical Drawing Program Templates In this exercise, you will be asked to insert pre-drawn images from templates available in ISIS Draw. You may have to complete this section on campus if you do not have ISIS draw on your computer since some drawing programs may not have the needed templates given below. Open ISIS Draw and select <Templates> in the menu bar. Select <Alpha-D-Sugars> and a menu of several alpha-D-sugar structures appear. Place the cursor on one of the bonds in the structure for the sugar [ADGLUCO] which is for alpha-D-glucose and mouse click. After mouse clicking, the structure should appear in ISIS Draw. Using the atom tool and add hydrogens to all the oxygens except the one in the ring. Import the structure into this document in the box below. Compound & Structure Compound & Structure [ADGLUCO] L-phenylalanine To import phenylalanine derived from the L-phenylalanine template, use the select <Templates> in the menu bar, the <L-Amino Acids>. Place the cursor on one of the bonds in the structure for the amino acid L-phenylalanine and mouse click. After mouse clicking, the structure should appear in ISIS Draw. Using ISIS Draw, add a hydroxyl group to the carbonyl and add hydrogens to the nitrogen to form complete structure of L-phenylalanine, them select all and import the entire image of L-phenylalanine into the box on the right above. partial structure of O phenylalanine R OH NH2 -OH added H's added Do the same for the following: add a p-orbital, and bicyclo[2.2.1]heptane found under their correspoinding templates. Structure Compound & Structure p-orbital bicyclo[2.2.1]heptane PART G - Copying and Pasting Data from a Data Base In this exercise, you are being asked to search on a compound using the internet and copying pasting that data into this document. For example, physical data for ethyl butanoate was copied and pasted from chemfinder into the box below. ethyl butanoate ethyl butanoate ester C6H12O2 O CH3CH2CH2 C OCH2CH3 Ethyl butyrate [105-54-4] Synonyms: Ethyl Butanoate; Butyric Ether; Butanoic acid ethyl ester; Ethyl n-Butyrate; natural ethyl butyrate; BUTIRATO DE ETILO; formula: C6H12O2 molar mass: 116.1596 melting point: -135.4 °C density: 0.878 g/mL boiling point: 252 °C at 0 mm refractive index: 1.392 solubility in water: 0.68 g/100 mL. Insoluble Flash point: 26 °C Comments: Colorless liquid with pineapple odor. Used in perfumes, rum Now do the same for the ethyl 2-bromo-2-methylpropionate. Use the internet to search on the compound. Searching by molecular formula will give a much broader search result for the given compound. To do a molecular search, be sure that you total the number of atoms—and hydrogens—correctly. Search by both molecular formula and name. ethyl 2-bromo-2-methylpropionate ester C6H11BrO2 O (CH3)2C C OCH2CH3 Br ethyl 2-bromo-2-methylpropionate Synonyms: _________ Formula: _________ molar mass: _________ melting point _________ °C density boiling point _________ °C refractive index _________ solubility in water _________ Flash point _________ Comments _________