To the first question, God has not revealed to us the exact details concerning a departed soul’s awareness of Earthly (temporal) events. So, while it ‘might’ be possible, it is rather unlikely because if the person is to enter heaven, they are either a) undergoing a purification of their soul in order to arrive at a perfect love of Almighty God or b) already in heaven where they are consumed in love & adoration of God. Their complete love of God would naturally extend to God’s children still on their Earthly pilgrimage.
To the second question: In God’s providential wisdom, he does permit some of the Saints in heaven extraordinary gifts of intercession concerning prayer requests from those still on Earth. Notable examples: the Blessed Mother, St. Joseph, & “fan favorite” St. Anthony (patron of lost things!).
That being said, it is highly encouraged for Christians to pray for their deceased loved ones and it never hurts to ask for their prayers in return. Our prayers will be answered in one way or another in accordance with the loving will of the Father.