The top picture shows 2-methylocta-4,6-dien-1-amine. The bottom shows an incorre

Question

The top picture shows 2-methylocta-4,6-dien-1-amine. The bottom shows an incorrect separation scheme of 2-methylocta-4,6-dien-1-amine.  

a.) Identify all of the mistakes in the incorrect separation scheme. Keep in mind that there will be more than one mistake in the scheme. For each mistake, give a detailed, scientific explanation of why it is incorrect.

b.) Draw a correct separation scheme to isolate 2-methylocta-4,6-dien-1-amine from the provided second molecule (NaCl). Make sure to indicate the phase of each chemical in every step (s, l, g, aq) AND write the separation technique used in each step (ie: vacuum filtration). The list below gives the reagents available in the lab. Use any of the reagents below to isolate the compounds. Remember that the simplest separation scheme is the best one. Try to avoid unnecessary steps.

10% aqueous NaOH, H2O, 5% aqueous NaHCO3, H3PO4, 6M HCl, anhydrous Na2SO4, 5% HCl, anhydrous MgSO4, Diethyl ether (ether), Saturated NaCl, CH3OH, Sodium borohydride (NaBH4), lithium aluminum hydride (LiAlH4), NaCl solid

Explanation / Answer

Separation of 2-methyl-4,6-octadiene-1-amine

1. Dissolve the mixture in diethyl ether. Add water to it and shake well.

NaCl dissolves in water.

2. Separate the organic layer containing the amine compound from the aqueous layer containing the NaCl salt.

3. Add anhydrous Na2SO4 to organic layer, filter and remove solvent to isolate 2-methyl-4,6,-octadiene-1-amine compound.

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