Summary, for end-users

If you use a Mac and ChemDraw, now is the time to learn the procedure to copy-and-paste ChemDraw elements for round-trip editing with MS Office 2016 documents. The changed occurred after Microsoft Office 2011 (Mac) and staying with that version of Office is not a viable long-term solution.

Here is the procedure to copy a ChemDraw object into MS Office 2016's Word or PowerPoint applications:

Step one is unchanged: copy (⌘+C).
Step two has changed: Paste as PDF (⌘+Control+V), instead of drag and drop or a simple paste, into an Office 2016 document.

With the end of the support lifecycle for Office 2011 on 10/10/2017, it may no longer be possible to install Office 2011 on newer versions of macOS.

http://blogs.cornell.edu/chemit/2017/08/22/macs-office-and-chemdraw-issue/

Prior cautions from Chemistry IT:

What you need to know: Mac's MS Office and ChemDraw

The procedure to copy-and-paste ChemDraw elements for round-trip editing with MS Office documents changed after Microsoft Office 2011 (Mac).

Most people in our department have up to this point managed this change by continuing to use Office 2011 for Word and PowerPoint. This strategy is not sustainable. To wit, Microsoft is dropping support of Office 2011 this October. And a forthcoming macOS version may not properly support Office 2011. Microsoft currently offers Office 2016, and no other version is available for download via Office 365 to personal computers.

There are no great options. One option is to learn to paste a ChemDraw object into Word or PowerPoint differently:

Step one is unchanged: copy (⌘+C).
Step two has changed:Paste as PDF (⌘+Control+V) instead of drag and drop into an Office 2016 document.

Status in Chemistry:

As of 1/17/17:

Researchers and others to reach out to, in person:

Person	Notes
Pete Wolczanski <ptw2>
Geoff Coates <gc39>
Dave Collum <dbc6>
Others?

Communication plan:

Method	Dates, aprox	Notes
Documented (wiki)	Fall 2016	Done, always being added to.
Newsletter (and News item)		Do "now", as of Jan 17, 2017
Talk about and meet with groups and individuals		See above table.
Computing Cmt's role?

ChemDraw 16:

Came out ~11/1/16:

The issues in the following section all apply to ChemDraw 16 as well as Chemdraw 15 and Chemdraw 15.1 on Apple MacOS computers.

http://www.cambridgesoft.com/software/overview.aspx
- http://www.perkinelmer.com/lab-solutions/resources/docs/DTS_012723B_01_ChemDraw_16.pdf
- http://www.cambridgesoft.com/literature/PDF/ChemDraw_16.pdf

To do:

What and where is the metadata embedded in files which can round-trip?

For both TIFF and(?) PDF.

What of Apple's applications?

Keynote. Heavily used by Geoff Coates, for example

Ensure the following compatibility behavior matrix is completed and accurate

For any more-recent version of MacOS (macOS), Windows, and ChemDraw.
Pay attention to version of MS Word (MS Office).
Similar cut-and-paste issue as with MathType, apparently.
Note: When creating pasting from CD into Windows (Office 16), it is possible to Paste Special from ribbon as a "CS ChemDraw Object" - double click image to round-trip edit
All with current version of ChemDraw (v16).

From ChemDraw to the following type of Word file:	Tested file on left on a Mac: Open in Word (Office 2011) => ChemDraw	Tested file on left on a Mac: Open in Word (Office 2016) => ChemDraw	Tested file on left on Windows: Word (Office 2016) => ChemDraw
Created/ edit on a Mac: Office 2011 (Word): METHOD 1 (default): Drag or cut-and-paste	OK	OK	FAIL
Created/ edit on a Mac: Office 2011 (Word): METHOD 2 (new): Paste Special => PDF	OK	OK	FAIL
Created/ edit on a Mac: Office 2016 (Word): METHOD 1 (default): Drag or cut-and-paste	FAIL	FAIL	FAIL
Created/ edit on a Mac: Office 2016 (Word): METHOD 2 (new): Paste Special => PDF	OK	OK	FAIL
Created/ edit on a Windows: Any Office version (Word): The basic METHOD (default): Drag or cut-and-paste	OK?	OK?	OK?

End of mainstream support (no more security patching) for Microsoft Office 2011 on October 2017

https://support.microsoft.com/en-us/lifecycle/search/?p1=15627

Also, support may end simply by virtue of new Mac OS's. For example, macOS 10.13 "High Sierra" has a new file system (APFS). Although APFS nominally may run any software newer than ~2009, might not for some specifically such as MS Office 2011. Example:

https://www.neowin.net/news/microsoft-says-office-for-mac-2011-will-not-be-supported-on-macos-1013-high-sierra?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+neowin-main+%28Neowin+News%29

Microsoft changed how pasting works in Office 2016 for the Mac

Issues with Round trip editing on Macs

For those using Office 2011 on Macs, it was possible to be able to drag and drop from Chemdraw into Word 2011 and drag and drop the image back into Chemdraw for editing. This is no longer the case for Office 2016.
Dragging and dropping from ChemDraw 15.1 to Word 2016 will paste an image into the Word document but the image will NOT be editable
Copying(⌘+C) and Pasting (⌘+V) will only paste text into Word(2016)
IMPORTANT: Opening a old Office 2011 file in Office 2016 and resaving it will not affect the images already in the document (you can drag them into Chemdraw for editing). However, anything dragged into Office 2016 will still not be editable

Workarounds:

Use paste as PDF instead of dragging and dropping. Copy the image from ChemDraw(⌘+C) and Paste it into Word 2016 using ⌘+Control+V instead of ⌘+V.

Supporting documentation

http://media.cambridgesoft.com/support/manuals/15_1/ChemOffice%20v15.1%20Release%20Notes.pdf

7 Known Issues, Limitations and Workarounds (as of download date 10/31/2016)

The following list describes the known issues, limitations, and workarounds for ChemOffice 15.1:

• When you copy any object from ChemDraw (Mac) and paste (default) in MS Word 2016, it pastes an MOL text version of that object instead of the original object view.

o Workaround: Use the 'Paste Special >> PDF option in MS Word to get the original object view pasted. This PDF object can be copied back to ChemDraw by maintaining all ChemDraw object properties.