This article shows the potential for using video responses to specific questions as part of the assessment process in an organic chemistry class. These exercises have been used with a postbaccalaureate cohort of 40 students, learning in an online environment, over a period of four years. A second cohort of 25 second-year students taking the organic chemistry course onsite has been using these exercises over a period of three years. The questions in this exercise require the students to use a molecular model kit. The problems presented to the students involve standard concepts in organic chemistry relating to geometric issues with molecules or organic reactions. This method of assessment allows the instructor to see a student's higher-order thinking on a particular topic to a greater degree than is generally afforded with clicker questions. Students are acclimated to this new environment for assessment through practice exercises that are evaluated and critiqued, but not counted towards a grade. A transition to similar exercises follows that counts towards the students' grades. Constructive feedback to the students for their nongraded and graded responses, as well as the types of errors and misconceptions they display in their videos, are also described.

Doceri software for iPad is useful for both synchronous online and asynchronous online delivery of chemistry course content. Using the Doceri wireless connection between the iPad and a personal computer that is running Adobe Connect, online synchronous instruction can be accomplished in which drawings can be completed by hand on the iPad. For asynchronous delivery, lectures can be easily recorded by Doceri on the iPad. As with synchronous lectures, the content on display can be easily annotated over, making it easy for the instructor to highlight materials while talking.

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.