Substitution 02 26 2015 Won t work because they hydroxide group would be the leaving group NaBr is the nucleophile but it work as written because hydroxide is a terrible leaving group It s a terrible leaving group Needs sulfuric acid because it makes the OH into a water good leaving group Now it can attack Substitution mechanisms o It protonates and makes it an water molecule sN1 and sN2 this will be sN2 because it is a primary alcohol One major change we will run the reaction at half scale Divide all the volumes and weights by 2 Keep the times the same though Second change When the reaction is over just do one extraction Put it in a 250 mL Erlenmeyer and add 150 200 mL of distilled water and 1 inch stir bar and mix for 10 minutes 1 bromobutane is more dense that water so it will be at the bottom o Big catch you need at least 2 mL of product o If you don t have two mL product you need to get teamed up with someone else and add your products together group work Safety focus Sulfuric acid make sure you use goggles o Will burn holes through your clothes How do we prove that we ve made 1 bromobutane We usually use MP for identity but it s a liquid so we can t do that We could do boiling point but that s hard to do We re going to do modern qualitative analysis and traditonal Calculate yield use a beaker instead of a weightboat Do the halide test traditional Getting structural information Collect rate data o How long does it take for the precipitate to form o SN1 3 2 1 o SN2 1 2 3 If the NaI test is faster and both forms a precipitate then you ve made what you want Modern Test IR infrared spectroscopy Links on the website C C C O C C C H o Different bonds require different amounts of energy o Will tell you what types of bonds are present in the molecule Fingerprint region from 1750 4000 o Unique region of the molecule no two molecules have the exact same fingerprint region o Take your IR analyze your functional group region o Compare fingerprint region of my IR with the one in the book o Whatever you take to the IR leaves with you don t leave shit How to take an IR around o Clean the IR twice Use the squirt bottle chem wipe Before and after o Don t wear gloves while typing DRY PRODUCT WITH SODIUM SULFATE o Prevents big OH peak o functional group region may be inconsistent 02 26 2015 02 26 2015