Example...
SegWit Address: 3Pih1gsGEufDcE3rnCvH7tSGxYCfAumr7N
Private Key: L31MGtLmx3RVomrNYkNzJqrd5h788GDkJpT6sTRhSu1rd2ZwWimr
Non-SegWit Address: 3FcdxBkv4Va8YLfyCe11pRsZ2uTki7DWvH
Private Key 1: L1QZg6Lqc8pH2RqWuEKzqv3rwjumQ2oMUyp4S8WPnZgWCnXPL4mu
Private Key 2: L3Qh439DtmJS1xKEe2tL7KG2niM4FWE6UvdJzs5DwdBqPZc8rrBe
Private Key 3: L5dhbsNKyzqPPgTFGe6kUVHibFv5QhoAhLJSVAqgTnyDXVimtm1E
Just looking at these addresses, how do we determine that 3Pih1gsGEufDcE3rnCvH7tSGxYCfAumr7N is SegWit and 3FcdxBkv4Va8YLfyCe11pRsZ2uTki7DWvH is not? And, if we can't determine, how do we decide whether to send SegWit Tx to these addresses or not?