If I have to guess for the second one I would say:
Emperor: Kao Tsung (1736 - 1795)
Reign title: Ch'ien-lung T'ung-pao
Qianlong
Shan-lung commemorative
Type A-2
CASH
Boo-Ciowan
KM# 389
Standard Catalog of World Coins 1701 - 1800, 4th edition, page 132
https://en.numista.com/catalogue/pieces1133.html
The picture on the coin page is not exactly the same as yours because as you can see, there are many varieties.
You have "DH#22.200 (Type A; 乾 with し radical)" or one of these types:
Type F1: し radical in 乾; cursive ciowan
Type F2: し radical in 乾; gap between oos in ᠪᠣᠣ
Type G1: し radical in 乾; protruding head ᠪᠣᠣ
Type G2: し radical in 乾; crude text; broad rims