This guide will help you assemble a set of different documents into a single, navigable PDF.  Examples of this might include professional portfolios or custom reading packets for students.  This page walks you through the basics, with several options for how you can arrange documents within a PDF.  You'll choose the options that best fits their purpose.  

For this project you will need Adobe Acrobat, that's part of the Creative Cloud suite available to Canisius College faculty and staff.  Acrobat is not a creator toolset, but rather software that allows you to compile, organize, and publish a PDF file that is itself a collection of content created in other file types.  Even Adobe does not suggest that you create content in Adobe Acrobat. 

So you'll also need a word processor, such as Microsoft Word, or Google Docs.  The files you wish to compile into a single PDF might be generated with various apps, such as AutoCAD, Excel, Google Drawings, or Canva, and they might be in formats such as .xlsx, .jpg, or Google Slides..  And you may include files that are in PDF format already, within your bigger PDF.  These may be files that were always digital, having been saved as PDFs in creation software (such as Word or Google Docs.)  Or, they can be scans of paper documents, that are essentially images saved in PDF format.  Adobe Acrobat can combine all of these into a single, navigable PDF document readable by anyone with a PDF reader application.  

PDF Files: the Basics

A PDF ("Portable Document Format") file offers a consistent format across PC or mobile devices that have a PDF reader.  There are many free PDF readers, including but not limited to Acrobat Reader, Adobe's free version of Acrobat.  A PDF file is not designed to be easily or extensively edited; it's a published product, rather than a draft.  Create your content in tools like Microsoft Word, Excel, Powerpoint, or Google Docs, Sheets, Slides, or Drawings.  Then, within Adobe Acrobat, you can add these together into a PDF file, and do final arrangement and organization, together with some minor edits, if needed. You can also scan in paper copies of documents, but born-digital documents are always best when working within Acrobat and PDFs. Major editing, reformatting, or adding additional content is best done in the original document files, such as .docx, or Google Docs, rather than in Acrobat.  Since it isn't built for extensive content creation, Acrobat's tools can be awkward and inefficient for major changes to the content within a PDF.  

Some PDF files are text, images, and graphics that are so indexed within the file that they can be extensively, albeit slowly, edited in Adobe Acrobat.  Others are crude scans that consist of a single image - like a photocopy or photograph - of something that happens to be saved within a PDF file.  With the latter, Adobe's tools may be able to do little or no editing, besides perhaps crude text overlay or annotations.  What Acrobat can do with a scanned document depends on the quality and condition of the paper original, and the circumstances of it's scanning.  

PDF files can be a combination of other files, that have either been amalgamated into a single PDF file, or simply stored and displayed together within a single PDF container.  For simplicity's sake, this guide shows you how to create the former, and that's what is meant here by "portfolio."

Organization

In compiling files or documents into a Navigable PDF, you should be aware of three navigation possibilities:

Bookmarks.  PDFs can contain a table of contents or organization that exists separate of any page within the document.  In Acrobat or Acrobat reader, this typically appears on the lefthand side when the Bookmarks tool is made visible.  These bookmarks are often also visible in other PDF readers.  By default, the separate file names appear as top-level headings, although they are editable.  With .docx files, subheadings will appear in their proper order and levels, but pages are not recognized.  With .pptx files, slides are listed.  The links to file names, headings, and slides in the Bookmarks list are rearrangeable, but this does not change their order, or any other content, within the files.  It can save time to just rely on this bookmark list, and dispense with the Table of Contents above, but this list may not be available if your readers elect to print out your PDF.  

Thumbnails. PDFs can contain a set of small "thumbnail" images of each page that together form a quick-navigation tool.  In Acrobat or Acrobat reader, this typically appears on the lefthand side when the Page Thumbnails tool is made visible.  This tool is probably less valuable for the reader, since the author can better recognize pages represented by the thumbnails, and only pages, rather than headings, are navigation choices here.

Table of Contents.  Although not a toolset built into Acrobat, you can create a dedicated Table of Contents page or pages, that include just page numbers or are actively linked to your content.  Unlike Bookmarks, the Table of Contents is a page within your portfolio, wherein the items in the Table list are hyperlinked to pages within the PDF.  When your readers click on items in the table of contents, they are taken to the corresponding page.  This presents a professional-looking product, and offers the option to create a document that is easily navigated if printed out, too.

Combining PDF Files 

Using Adobe Acrobat, assembling files into a PDF file is fairly easy.  For many common file types, such as .docx, you may not even need to save or export the file in .pdf format since Acrobat can read various file types when compiling them into a PDF file.   

In Acrobat, to add files to a new PDF file, click Tools and choose "Combine Files.  If you then click "Add Files," you'll see an Explorer or Finder window, but you can also just drag and drop files into this webpage to upload them.

It may take several seconds or even minutes for Adobe to generate thumbnail images of your files on the following page.  Once this is done, you can quickly rearrange the order of the files by dragging and dropping.  You can also do this later on, but it's quicker to do it now.

Once you are satisfied with their order, click "Combine," and Adobe will generate a single PDF file using these documents.  

Organizing your Contents

Once you have files assembled into a PDF file, you can rearrange them in several ways.  Click the "Organize Pages" icon on the right toolbar.  (Or, click Tools → Organize Pages.)

Adding Another File

If you forgot to add a file, you can still do so after having created the PDF file.  Recognize, however, that if you have many additions, and you have already created a Table of Contents, there are many more steps involved and you may be better off simply creating a new Table of Contents page, and recompiling a new PDF file.

To add a file to a PDF, on the Organize Pages screen, click Insert at the top, and choose "From File..."

You can then find and add the file or files from your Hard Drive.  

Rearranging Files

On the Organize Pages screen, you can drag and drop pages into a different order.  If you hold down the SHIFT key, you can click/select multiple pages, which can make moving them easier.

Rotating Pages

Rotate pages by clicking on the page to highlight it.  A small menu appears; click the circle-arrow icons to rotate the page image in either direction.  

If, after having assembled your portfolio, you find that you need to add an additional document, this is doable but as noted above, it is not as efficient as assembling everything beforehand.  Adding the file to the portfolio is easy; editing your Table of Contents is more challenging.

While viewing your Table of Contents, click the "Edit PDF" Icon on the right.

This will create a text box around your Table of Contents list.  You can click inside, and type in the new item, just as you would in Word.  

Then, click "Link" on the upper toolbar.

Adobe highlights the spaces where links work in the Table of Contents.  Now that you added a line (or lines) to the Table, the links going to various pages, below the new additions you typed into the Table of Contents, do not properly light up with their corresponding text.  Rearrage them accordingly by clicking and dragging the link spaces.  

Again, click "Link" on the upper toolbar, and choose "Add/Edit Web or Document Link."  

Click and drag with your mouse, to create a new link space.  Follow the steps in the dialog/pop-up boxes to create the link:

• For Link Type use "Invisible Rectangle."
• Link Action should be "Go to a page view."
• Follow Acrobat's instructions to establish the page to which the new link will go.

As you can see there's a lot of steps and some careful mouse-work to edit the Table of Contents in Adobe.  For this reason, try to assemble everything you need, and build your Table of Contents and Section Pages in MS Word, first.  If you have extensive edits to make to a Portfolio, consider recompiling it a new PDF file.  

When combining files into a PDF file, it's important to remember that Acrobat is not a content creation tool, so much as a document publishing tool.  The distinction is important, because you wish to create the final outline or skeleton of your PDF file in Microsoft Word, and add it to Adobe Acrobat, together with PDF files.  Since editing files in Acrobat is not efficient, you want to avoid having to make changes to the PDF once it's assembled.  If changes to the contents, organization, and the Table of Contents itself are extensive, you may find it's easier just to recompile your files into another PDF, rather than attempt to make changes to the Table of Contents within Acrobat.  

Build the Bookmarks List

In most cases Acrobat will auto-generate a set of bookmarks when you combine the files.  File names will be the major headings, but there may be additional sub-headings, for example generated from the headings within the files, or individual slides in a slidedeck.  

If you right-click on a bookmark, you get a variety of different options, including to delete or change it's destination (where it goes when a reader clicks it.)  Probably most useful is "rename," since you may want more descriptive headings than your file names.  

You can also manually add bookmarks:

Create a Table of Contents

Creating PDF Files or Pages using Microsoft Word

In most Word Processors, you can save or export a file in .PDF format.  Even Google Docs, 

Here, we'll discuss the simplest method for creating a Navigable PDF file that includes various documents.  There are more complicated methods that potentially provide more and better options, and you can review them by clicking the options below.

First, 

https://www.youtube.com/embed/-yUS89t3Alg

Is it possible to enact this plan?  Create a skeletal document using Microsoft Word, that includes a clickable TOC.  The TOC only highlights pages where the faculty member will provide some sort of introductory page.  So when you assemble the final portfolio, you put the scanned or otherwise collected documents in among these introductory pages, such that the clickable TOC is entirely built in Word, rather than having to fuss with it in Adobe.  It's doable, and editable in Acrobat, because it appears that Acrobat converts the .docx internal links to PDF Document Links.  But, two caveats:

• Don't add page numbers in Word.  Once you add the other content in between, they need to be updated anyway.
• if you need to edit the resulting PDF it's a pain, because you would need to shift the links down, and create new ones in the TOC, which is complicated and not for the impatient.  

PDF Portfolio feature in Acrobat

In this mode Acrobat creates a PDF container that includes files in their original format.  Thus, a .pptx file is still editable (and probably extractable) as .pptx.  When viewed in Acrobat Reader, these files are still in their original format.  This could cause complications for less patient readers, since A-Reader does not automatically preview these files.  Adobe purports to include web pages, but in my test it handled https://www.canisius.edu/academics/office-academic-affairs/academic-institutes-and-centers/center-online-learning-innovation poorly.  

In short, this is too complicated for most who might read a PDF portfolio, and would result in an untenable support burden for COLI.  

Organize Documents

Now that your documents are installed, 

Rearranging Files

Rotating Pages

Adding Page Numbers to a PDF

Is it possible to have Acrobat create the page numbers, and then after that, add the TOC?  So that you get the entire document exactly the way you want it, and then as a last step add the TOC?  

Creating a Table of Contents for a PDF Document

Create the Table of Contents using Microsoft Word

Creating a Clickable Table of Contents using Adobe Acrobat

Resources

https://helpx.adobe.com/support/acrobat.html