Apache ProxyPass/ProxyPassReverse to IIS

You'll need mod_ssl, mod_proxy and optionally mod_rewrite. Depending on your distribution and Apache version you may have to check if mod_proxy_connect and mod_proxy_http are loaded as well.

The directives for enabling SSL proxy support are in mod_ssl:

<VirtualHost 1.2.3.4:80>
    ServerName foo.com
    SSLProxyEngine On
    SSLProxyCheckPeerCN on
    SSLProxyCheckPeerExpire on
    ProxyPass / https://secure.bar.com
    ProxyPassReverse / https://secure.bar.com
</VirtualHost>

IIRC you can also use:

    RewriteRule / https://secure.bar.com [P]    # don't forget to setup SSLProxy* as well

Hmmm. Try migrating to a mod_proxy_ajp config first (assuming you have it included - it's a stock module with many modern Apache installs) to see if that does it. First, make sure your port 8009 AJP connector is uncommented in Tomcat's server.xml:

<Connector enableLookups="false" port="8009" protocol="AJP/1.3" redirectPort="8443" URIEncoding="UTF-8" />

Then set up Apache pretty much the same; you might consider using a one-node pool so that you can have it "see" the jsessionid. Then add some rewrite rules to mask the directory name:

RewriteEngine on
RewriteCond %{REQUEST_URI} !^/jetwick/
RewriteCond %{REQUEST_FILENAME} !-f
RewriteCond %{REQUEST_FILENAME} !-d
RewriteRule ^(.*)$ /jetwick/$1

ProxyPass /jetwick/ balancer://local/ stickysession=JSESSIONID|jsessionid
<Proxy balancer://local>
  BalancerMember ajp://127.0.0.1:8009
</Proxy>

I don't have a Tomcat engine handy right now to test that, but it looks right when I read it... :) You might need a [PT] flag on the rewriterule, play with it and see what you get.