Vrenna looked it and smiled.
( Vrenna ( ( ( ( looked it ) and ) smiled ) . ) )
(ROOT (S (NP (NNP Vrenna)) (VP (VP (VBD looked) (NP (PRP it))) (CC and) (VP (VBD smiled))) (. .)))
Vreanna wore a pleased expression when she saw it. 
( Vreanna ( ( ( wore ( a ( pleased expression ) ) ) ( when ( she ( saw it ) ) ) ) . ) )
(ROOT (S (NP (NNP Vreanna)) (VP (VBD wore) (NP (DT a) (ADJP (JJ pleased)) (NN expression)) (SBAR (WHADVP (WRB when)) (S (NP (PRP she)) (VP (VBD saw) (NP (PRP it)))))) (. .)))