Functional Relationships of Alcohols

Alcohols are versatile compounds. As shown in the diagram on the right, they can be converted into many other functional classes (red arrows), and can in turn be made from many other fuctional groups (green arrows). Shown below is a list of 16 different reagents and reaction conditions which, if selected and used in an appropriate manner, will produce the conversions shown in the diagram.

Reagents & Reaction Conditions

1.   Na or NaH in an ether solvent.
2.   Dilute aqueous acid (H3O+).
3.   Reaction with a 1°-alkyl halide or tosylate (R-X).
4.   Reaction with HBr, HI, HCl+ZnCl2, SOCl2, PBr3 or PCl5
5.  Sulfuric acid or phosphoric acid (conc.) and heat.
6.   Mg in ether.
7.  i) LiAlH4 in ether; ii) H3O+
8.   NaBH4 in ethanol.
9.   Na2Cr2O7 in aqueous sulfuric acid (Jones' reagent).
10.   CrO3 + pyridine + HCl in CH2Cl2 solution (PCC).
11.   An aryl sulfonyl chloride (ArSO3Cl) in pyridine.
12.   i) Hg(OAc)2 in H2O; ii) NaBH4 in ethanol.
13.   i) B2H6 in ether; ii) H2O2 in aqueous sodium hydroxide.
14.   Heating with a carboxylic acid and a strong acid catalyst.
15.   A carboxylic acid anhydride or acyl chloride in pyridine.
16.   Refluxing NaOH solution.

If you click on the name of one of the ten functional groups surrounding alcohols in the diagram, a question concerning the choice of conditions for that conversion will appear. The question will take the form shown below, with two or three answer boxes positioned for the alcohol class (1 º, 2 º or 3 º ), the reagents & conditions for the forward reaction, and in some cases the reverse transformation back to the alcohol. If the selected transformation will occur only for certain classes of alcohol reactants, enter a number (1, 2 or 3) corresponding to the chosen class in the box following the word "alcohol". If all classes will undergo the specified reaction leave this answer box empty. For the boxes above (and below) the arrow(s) enter numbers (1 to 16) corresponding to the reagents and conditions listed above. For a several step reaction enter the numbers in the order the reactions are to be carried out.. No more than three steps should be designated; and if several reaction sequences are feasible, enter only one.
Do not enter punctuation or spaces.

Alcohol   [Class] [Reagents]

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