If you used the fmsadmin command line CERTIFICATE CREATE command to generate the serverRequest.pem file you will then need to use the fmsadmin CERTIFICATE IMPORT command to import the certificate. Chapter 7 of the FileMaker Server Getting Started guide has all the details.
If you didn't use the fmsadmin command to generate the certificate request then you can try using the Admin Console Import Certificate command found in the Database Server > Security tab. Make sure you're using a compatible SSL in both cases:
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We created this step by step guide in the early days of v14 that you may find helpful, it does include the certificate location:
By the way, I appreciate you are using a Mac, but most of the information is Filemaker specific rather than platform specific.