3-Chloro-1-pentene reacts with sodium ethoxide in ethanol to produce 3-ethoxy-1-pentene. The reaction is second order, first order in 3-chloro-1-pentene and first order in sodium ethoxide. In the absence of sodium ethoxide, 3-chloro-1-pentene reacts with ethanol to produce both 3-ethoxy-1-pentene and 1-ethoxy-2-pentene. The first reaction proceeds via an mechanism. The stereochemistry of the product is . The second reaction proceeds via an mechanism. The stereochemistry of 3-ethoxy-1-pentene is . The stereochemistry of 1-ethoxy-2-pentene is . For the second reaction, draw the structure of the intermediate's resonance contributor that leads to the formation of 1-ethoxy-2-pentene.