I think this may solve your problem:
in config/application.rb:
config.autoload_paths << Rails.root.join('lib')
and keep the right naming convention in lib.
in lib/foo.rb:
class Foo
end
in lib/foo/bar.rb:
class Foo::Bar
end
if you really wanna do some monkey patches in file like lib/extensions.rb, you may manually require it:
in config/initializers/require.rb:
require "#{Rails.root}/lib/extensions"
P.S.
Rails 3 Autoload Modules/Classes by Bill Harding.
And to understand what does Rails exactly do about auto-loading?
read Rails autoloading — how it works, and when it doesn't by Simon Coffey.