A free online social annotation platform, Perusall, was incorporated into a flipped organic chemistry course sequence. The platform provides an interactive chat enhanced with social media features that facilitates student engagement with each other as they watch videos in an asynchronous format. This technology transforms how students watch flipped content from an isolated experience to an active, collaborative one in which they can ask questions, discuss ideas, and get feedback. Student compliance was high, and survey responses about the technology were generally positive, with students reporting that it improved their understanding, decreased their boredom when watching videos, and made them more comfortable in asking questions. The quality of the conversations on Perusall was typically better than what we have been able to stimulate in class, likely because of the low-stakes environment of commenting in the chat. Analytics revealed that, on average, students actively watched each video for a time period that was 3 times the video length, with shorter videos resulting in higher relative viewing times compared with lengthier videos. Overall, this technology offers a new tool for instructors seeking to enhance student learning experiences in flipped classrooms by facilitating social, collaborative interactions with videos.