Itemized deductions (Schedule A) is not supported in the TurboTax Free edition.
The standard deduction for 2016 is $6,300 Single or Married Filing Separately; $9,300 Head of Household; and $12,600 for Married Filing Jointly.
You would need deductions that add up to more than that for the itemized option to be advantageous.
Additionally, certain deductions are limited. For instance, medical expenses usually must be more than 10% of your Adjusted Gross Income (AGI) before they even start to count and job expenses don't count until they are over 2% of your AGI.