The prepaid money that was received in 2020 for 2021 school living expenses should be reported in the year that it was received (2020), regardless of when it was used. This is because of something called the matching principle. See IRS Pub 538 for more information.
The amounts that were given to him for rent and living expenses should not be reported together with the funds for books. This is because books are considered necessary for education; living expenses and food is something everyone needs regardless of whether they are receiving a college education or not. Those items are considered "income" for federal tax purposes, and are taxable as such. The books are not.
To enter your scholarship income in TurboTax, in your return, go to Federal Taxes, Deductions & Credits, Education and the program will walk you through the information about your scholarship income, to determine what's taxable.
Here is a TurboTax article with more information about scholarships.