Whats in a medicine

Nota:

•    Name ends in ‘ol’ eg ethanol   

1. Primary Alcohol

   Nota:

   •    The alcohol group is attached to a carbon which is only attached to one other carbon atom   
   1. ROH
   2. Mild Oxidation
      1. Aldehyde

         Nota:

         •    Name ends in ‘al’ eg ethanal   
         1. RCHO
      2. Acidified Potassium Dichromate

         Nota:

         •    Goes from orange to green   
      3. Distillation Equipment

         Nota:

         •    Products evaporate, separate and the condense   
   3. Further Oxidation
      1. Carboxylic Acid

         Nota:

         •    Name ends in ‘oic acid’ eg ethanoic acid   
         1. RCOOH
         2. Acidity

            Nota:

            •    Carboxylic acids are the most acidic and will react with carbonates and hydroxides. Phenols are slightly acidic but only react with hydroxides. Alcohols are not very acidic and won’t react with either   
            1. Form 'carboxylate ion

               Nota:

               •    Carboxylate anion is stabilised by the negative charge been delocalised between the oxygen atoms   
      2. Acidified Potassium Dichromate

         Nota:

         •    Goes from orange to green   
      3. Reflux equipment

         Nota:

         •    Reactants and products evaporate and then condense and drip back down into the reaction vessel. This avoids the loss of volatile reactants and products.   
2. Secondary Alcohol

   Nota:

   •    The alcohol group is attached to a carbon which is attached to two other carbon atoms   
   2. Oxidation

      Nota:

      •    Secondary alcohol can’t further oxidise   
      1. Acidified Potassium Dichromate

         Nota:

         •    Goes from orange to green   
      2. Reflux or Distillation Equipment

         Nota:

         •    Reflux equipment will get a better yield   
      3. Ketone

         Nota:

         •    Name ends in ‘one’ eg propanone   
3. Tertiary Alcohol

   Nota:

   •    The alcohol group is attached to a carbon which is attached to three other carbon atoms   
   2. Will not oxidise

1. Carboxylic Acid + Alcohol
2. Catalyst: Conc. sulphuric acid
3. Fruity Smell
4. RCOOR

2. Neutral Iron (III) chloride turns purple
3. Forms esters with acyl chlorides
   1. RCOCl
4. Acidity

   Nota:

   •    Carboxylic acids are the most acidic and will react with carbonates and hydroxides. Phenols are slightly acidic but only react with hydroxides. Alcohols are not very acidic and won’t react with either   
   1. Form phenoxides with strong bases

      Nota:

      •    Phenoxide anion is stabilised by the negative charge been drawn into the delocalised benzene ring   

1. Rearrangement

   Nota:

   •   100% atom economy   
2. Addition

   Nota:

   •    100% atom economy   
   1. Nucleophilic Addition
3. Substitution
4. Elimination
5. Condensation

1. Is it safe?
2. Does it work?
3. Is it better than existing treatments?

1. IR Spectra

   Nota:

   •    Using the data sheet identify peaks (normally troughs) quoting the wavenumber of the peak and what it is. Also discuss peaks that are not there as well. Key peaks to look for are carbonyls, carbon-oxygen and OH groups that are alcohols or carboxylic acids (broad)   
2. Mass Spec

   Nota:

   •    Identify the common fragments listed below remembering if they are on the spec they are positive, the other fragment is not charged and does not show up.   CH3+ = 15 C2H5+ = 29 C6H5+ = 77 OH+ = 17  
   1. High Resolution

      Nota:

      •    High resolution MS is precise to 4dp enabling accurate isotopic and molecular masses to be identified. Peaks are clearly distinguished and don’t merge into each other   
3. Thin-Layer Chromatography

   Nota:

   •    Prepare a model method and diagram for the exam