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Adjust oven rack to middle position and heat oven to 350 degrees. Lightly spray bottom and sides of 9-inch springform pan with vegetable oil spray. Using paper towel, wipe sides of pan, leaving only thin film of oil. Combine olive oil and chocolate in bowl and microwave until chocolate is melted, about 1 minute. Stir until combined. Whisk flour, cocoa, baking powder, baking soda, and salt together in medium bowl.
Whisk 1 cup sugar, eggs, and yolk in large bowl until combined. Whisk in olive oil mixture until fully incorporated. Whisk in milk until incorporated. Whisk in flour mixture until smooth. Transfer batter to prepared pan; sprinkle remaining 2 tablespoons sugar over surface. Secure pan clip with your hand to prevent pan from opening and rap pan gently on counter to dislodge surface air bubbles. Bake until skewer inserted diagonally into crack and aimed toward center of cake comes out with few crumbs attached, 30 to 35 minutes.
Transfer pan to wire rack and let cake cool completely, about 2 hours. Run knife around edge of cake to loosen. Remove side of pan. Cut cake into wedges and serve. (Leftover cake can be wrapped and stored at room temperature for up to 3 days.)