Here is a first stab at producing this layout in the Table of Contents.
The titletoc package provides the powerful \titlecontents macro that allows one to change ToC entries for sectional headings mid-document. In the MWE below, two new macros are defined using the xparse interface \NewDocumentCommand. Specifically, they are \rtocstuff[<gap>]{<content>}[<width>] and its complement \ltocstuff[<width>]{<content>}[<gap>]. The former typesets <content> on the right of the ToC group defined by the chapter, while the latter typesets <content> on the left. <width> (default 150pt) specifies the width of <content> (using an overlap to allow for varied widths), while <gap> specifies the distance between <content> and the ToC.
For the sake of illustration, I've added
\rtocstuff{\includegraphics[valign=T,width=50pt]{tiger}}%
to each odd chapter, and
\ltocstuff{\includegraphics[valign=T,width=50pt]{tiger}}%
to the even chapter.
The main idea behind the two commands is to adjust the ToC margins when typesetting a chapter ToC. This is done by using boxes of fixed length (for accurate spacing and horizontal alignment). Also, <content> is \smashed so that it can protrude up/downward into the sectional ToC headings.
The current implementation could be considered slightly primitive, but it works with some trickery with adjustbox's valign=T option. Additionally, the alignment within the overlapped box that holds <content> can be optimized, as well as the ToC layout. It also only modifies chapter and section ToC styles and nothing else. So if you need subsections (or others), they need to be included for consistency. But this may all depend on the context. The heavily commented code below will give you a good indication of what should/can be modified to obtain the desired output.
\documentclass{book}
\usepackage[latin1]{inputenc}
\usepackage[T1]{fontenc}
\usepackage{geometry}% http://ctan.org/pkg/geometry
\usepackage{titletoc}% http://ctan.org/pkg/titletoc
\usepackage[export]{adjustbox}% http://ctan.org/pkg/adjustbox
\usepackage{xparse}% http://ctan.org/pkg/xparse
\NewDocumentCommand{\rtocstuff}{O{20pt} m O{150pt}}{% \rtocstuff[<gap>]{<content>}[<width>]
\titlecontents{chapter}
[0pt]% left margin indent
{\bigskip\bfseries}% chapter ToC formatting
{\makebox[1.5em][l]{\thecontentslabel}}% chapter label (numbered)
{\hspace{1.5em}}% chapter label (unnumbered)
{\titlerule[1pc]{.}% dotted contents line
\thecontentspage% ToC page number
\hspace{#1}% gap between page number & <content>
\smash{% remove vertical height of image
\raisebox{1.5ex}{% align with top of character
\hspace{#3}% space for <content>
\llap{% left overlap
#2% actual <content>
}}}}%
\titlecontents{section}
[0pt]% left margin indent
{\normalfont}% section ToC formatting
{\hspace{1.5em}\makebox[2.3em][l]{\thecontentslabel}}% section label (numbered)
{\hspace{3.8em}}% section label (unnumbered)
{\titlerule[1pc]{.}% dotted contents line
\thecontentspage% ToC page number
\hspace{#1}% gap between page number & <content>
\hspace{#3}% gap for <content>
}
}
\NewDocumentCommand{\ltocstuff}{O{150pt} m O{20pt}}{% \ltocstuff[<width>]{<content>}[<gap>]
\titlecontents{chapter}
[0pt]% left margin indent
{\bigskip\bfseries}% chapter ToC formatting
{\smash{% remove vertical height of image
\raisebox{1.5ex}{% align with top of character
\rlap{% right overlap
#2% actual content
}\hspace{#1}% space for <content>
}}%
\hspace{#3}% gap between <content> and ToC entries
\makebox[1.5em][l]{\thecontentslabel}}% chapter label (numbered)
{\smash{% remove vertical height of image
\raisebox{1.5ex}{% align with top of character
\rlap{% right overlap
#2% actual <content>
}\hspace{#1}% space for <content>
}}%
\hspace{1.5em}}% chapter label (unnumbered)
{\titlerule[1pc]{.}% dotted contents line
\thecontentspage% ToC page number
}
\titlecontents{section}
[0pt]% left margin indent
{\normalfont}% section ToC formatting
{\hspace{#1}% space for <content>
\hspace{#3}% gap between <content> and ToC entries
\hspace{1.5em}\makebox[2.3em][l]{\thecontentslabel}}% section label (numbered)
{\hspace{3.8em}}% section label (unnumbered)
{\titlerule*[1pc]{.}% dotted contents line
\thecontentspage% ToC page number
}
}
\usepackage{lipsum}% http://ctan.org/pkg/lipsum
\begin{document}
\contentsmargin{0pt}% Remove right margin in ToC
\tableofcontents
\rtocstuff{\includegraphics[valign=T,width=75pt]{tiger}}
\chapter{Coordinates of points}
\section{Rectangular coordinates} \lipsum[1]
\section{Projections of a segment on the axes} \lipsum[2]
\section{Distance between two points} \lipsum[3]
\section{The mid-point of a segment} \lipsum[4]
\section{Division of a segment in any ratio} \lipsum[5]
\section{Oblique coordinates} \lipsum[6]
\ltocstuff{\includegraphics[valign=T,width=75pt]{tiger}}
\chapter{The locus of an equation}
\section{First illustrations} \lipsum[1]
\section{Curve plotting} \lipsum[2]
\section{Test that a point lie on a curve} \lipsum[3]
\section{Intercepts} \lipsum[4]
\section{Points of intersection of two curves} \lipsum[5]
\section{Oblique coordinates} \lipsum[6]
\rtocstuff{\includegraphics[valign=T,width=75pt]{tiger}}
\chapter{The straight line}
\section{Equation in terms of point and slope} \lipsum[1]
\section{Line through two points} \lipsum[2]
\section{The general equation of first degree} \lipsum[3]
\section{Parallel and perpendicular lines} \lipsum[4]
\section{Angle between two lines} \lipsum[5]
\section{Distance from a point to a line} \lipsum[6]
\end{document}
Finally, since this example has a duplicate tiger at each chapter, you could also automate this using some help from the etoolbox package, by patching \chapter:
\usepackage{etoolbox}% http://ctan.org/pkg/etoolbox
...
\preto{\chapter}{%
\ifodd\thechapter
\ltocstuff{\includegraphics[valign=T,width=75pt]{tiger}}
\else
\rtocstuff{\includegraphics[valign=T,width=75pt]{tiger}}
\fi
}
The above addition produces the same output as before. However, you might not be interested in such an implementation, since the images would ideally like to change from one chapter to the next, to showcase some conceptual idea conveyed in that particular chapter.
You'll also notice that I've completely redefined the chapter and section formatting using the notation provided by titlesec. For example, the 1pc dotted contents line. This, as always, can be modified to match the regular book document class more closely.
:-)– Paulo Cereda Oct 14 '11 at 11:36