See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Bond Length Analysis **Identify the bonds:** - **(w)**: $C-O$ single bond (in $-CH_2-CH_2-O-H$) - **(x)**: $C-O$ single bond (in $-CH_2-C(=O)-O-H$) - **(y)**: $C=O$ double bond (carbonyl) - **(z)**: $C=O$ double bond (carbonyl in ketone) **Bond length principle:** Double bonds are shorter than single bonds. $$\text{Bond order: } C=O > C-O$$ Therefore: $y, z > w, x$ (both double bonds are shorter than both single bonds) **Distinguish between single bonds (w vs x):** - **(x)**: $C-O$ is **adjacent to carbonyl** ($-O-H$ attached to carboxyl carbon). The carboxyl carbon is sp² hybridized and electron-withdrawing, **pulling electron density** from the adjacent $C-O$ bond, making it **stronger and shorter**. - **(w)**: $C-O$ is in a simple alcohol ($-CH_2-O-H$). The carbon is sp³ hybridized with **less electron withdrawal**, making this bond **longer**. $$w > x \text{ (alcohol } C-O \text{ is longer than carboxylic acid } C-O\text{)}$$ **Distinguish between double bonds (y vs z):** - **(y)**: $C=O$ is in carboxylic acid with resonance stabilization (single bond character increases due to $O-H$ resonance) - **(z)**: $C=O$ is in ketone (pure double bond, no resonance) $$z > y \text{ (ketone } C=O \text{ is shorter due to pure double bond character)}$$ **Final order:** $$w > x > y > z$$ **The answer is (c): $w > x > y > z$**