Which of the following items cannot be deducted as an itemized expense on Schedule A?

Schedule A of the IRS Form 1040 is specifically utilized for itemizing deductions related to various personal expenses. Among the options provided, traditional IRA contributions cannot be deducted as an itemized expense on Schedule A because they are considered "above-the-line" deductions. This means that they are subtracted from gross income to determine adjusted gross income, rather than being an itemized deduction.

In contrast, health insurance premiums, property taxes, and mortgage interest payments are all eligible to be deducted as itemized expenses on Schedule A. Health insurance premiums can be deducted if they exceed 7.5% of your adjusted gross income (AGI), property taxes are fully deductible, and mortgage interest is also deductible on amounts paid for a primary residence or second home, subject to certain limitations. Therefore, understanding the classification of these expenses is crucial for tax planning and maximizing deductions on individual tax returns.