What is the ruling on praying behind an undesirable Imam?

It is permissible to pray behind an Imam who is undesirable for committing religious violations, and it is disliked for such an Imam to lead the prayer. Still, If he was undesirable for a personal, or a worldly matter, then such argument doesn’t hold water. And Allah Knows Best.

Is wearing a cap permissible for boys, or girls?

All Perfect Praise is due to Allah, The Lord of The Worlds.

In principle, anything is permissible sol long as there is no Sharia evidence prohibiting it, thus wearing the cap by boys is permissible as long as it isn`t done in imitation of the disbelievers. Moreover, a Muslim woman should avoid all that which attracts the attention of men because whatever leads to the forbidden is forbidden. And Allah Knows Best.

Is it permissible for a Muslim physician to specialize in gynecology obstetrics, and what is the ruling on working as such?

Some fields of knowledge are an individual duty while others are a collective one, and specializing in gynecology obstetrics is a collective duty. However, if there were female physicians to treat women, then there is no need for a male gynecology obstetrics specialist to look at women`s Awrahs (private parts) except in necessary situations since the jurisprudential maxim says:” Necessity must only be assessed and answered proportionately.” And Allah Knows Best.

A woman used contraceptive pills, and her menses exceeded (15) days, is it permissible for her to fast?

The maximum of menstrual blood is (15) days, but if it exceeded that due to a medication, or the like, then it is Istihadah (bleeding outside the monthly period), and in this case she should perform Ghusl (ritual bath), pray, and fast. Moreover, she is obliged to make up for the missed fasting days which exceeded her regular menses. And Allah Knows Best.