Firstly I would get the student to draw out the structure of the alcohol and check whether they were able to place the alcohol groups and side chains in the right place on the chain. Then I take would them through the following steps to name the alcohol: 1. Identify the longest chain and what the main part of the name is using the naming prefixes (meth- eth- pro- but- pent- etc) answer: pentane 2. Work out how to number the chain so that the alcohol substituent has the lowest number answer: alcohol at position 2 rather than 4 3. Recall that with an alcohol, this changes the end of the name to -ol, and that the number is placed before the -ol answer: pentan-2-ol 4. Work out the position of the side chain and what this is called again using the naming prefixes answer: methyl on position 4 5. add this final part onto the begining of the name answer: 4-methylpentan-2-ol