$(1)\quad(p\Leftrightarrow\neg\,r)$
This can be transformed using the equivalence tautology $(p\Leftrightarrow q)\iff(p\Rightarrow q)\land(q\Rightarrow p)$.
$(2)\quad((p\Rightarrow\neg\,r)\land(\neg\,r\Rightarrow p))$
This can be transformed further using the implication tautology $(p\Rightarrow q)\iff(\neg\,p\lor q)$.
$(3)\quad((\neg\,p\lor \neg\,r)\land(\neg\neg\,r\lor p))$
You can distribute this further as...
$(4)\quad(((\neg\,p\lor\neg\, r)\land\neg\neg\,r)\lor((\neg\,p\lor\neg\, r)\land p)))$
$(5)\quad(((\neg\,p\land\neg\neg\,r)\lor(\neg\, r\land\neg\neg\,r))\lor((\neg\,p\land p)\lor(\neg\, r\land p)))$
Anything of the form $(\neg\,p\land p)$ is a contradiction, therefore always false.
$(6)\quad(((\neg\,p\land\neg\neg\,r)\lor\bot)\lor(\bot\lor(\neg\, r\land p)))$
You can always disjunct with $\bot$ without changing the value, so you can leave it out.
$(7)\quad((\neg\,p\land\neg\neg\,r)\lor(\neg\, r\land p))$
Now you can replace the two and get:
$(8)\quad((\neg\, r\land p)\lor(\neg\,p\land\neg\neg\,r))$