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Chapter 9: Problem 60

Benzaldehyde, \(\mathrm{C}_{7} \mathrm{H}_{6} \mathrm{O}\), is a fragrant substance responsible for the aroma of almonds. Its Lewis structure is O=Cc1cccc(C=O)c1 (a) What is the hybridization at each of the carbonatoms of the molecule? (b) What is the total number of valence electrons in benzaldehyde? (c) How many of the valence electrons are used to make \(\sigma\) bonds in the molecule? (d) How many valence electrons are used to make \(\pi\) bonds? (e) How many valence electrons remain in nonbonding pairs in the molecule?

Short Answer

Expert verified
(a) All carbon atoms in benzaldehyde have sp2 hybridization. (b) There are 40 valence electrons in total. (c) 24 valence electrons are used to make σ bonds. (d) 4 valence electrons are used to make π bonds. (e) 12 valence electrons remain in nonbonding pairs.

Step by step solution

01

(a) Hybridization at each carbon atom

To determine the hybridization at each carbon atom, we can first count the number of sigma bonds and lone pairs around each carbon atom. - Carbon1 (C1): double bond with O, single bond with C2 => hybridization = sp2 - Carbon2 (C2): single bonds with C1, C3, C6 => hybridization = sp2 - Carbon3 (C3): single bond with C2, C4, H => hybridization = sp2 - Carbon4 (C4): single bond with C3, and C5 => hybridization = sp2 - Carbon5 (C5): single bond with C4, C6, and H => hybridization = sp2 - Carbon6 (C6): single bond with C2, C5, H => hybridization = sp2 So, all carbon atoms have sp2 hybridization in the benzaldehyde molecule.
02

(b) Total number of valence electrons

To find the total number of valence electrons, we need to sum up the valence electrons for every atom in the molecule. For benzaldehyde, we have: 7 Carbon atoms: (7 atoms × 4 valence electrons per carbon) = 28 valence electrons 6 Hydrogen atoms: (6 atoms × 1 valence electron per hydrogen) = 6 valence electrons 1 Oxygen atom: (1 atom × 6 valence electrons per oxygen) = 6 valence electrons Total valence electrons: 28 + 6 + 6 = 40 valence electrons
03

(c) Valence electrons used to make σ bonds

In benzaldehyde, we have the following σ bonds: 6 σ bonds between carbon and hydrogen 5 σ bonds between carbon and carbon 1 σ bond between carbon and oxygen Total σ bonds: 6 + 5 + 1 = 12 σ bonds Every σ bond uses 2 valence electrons, so to calculate the number of valence electrons used for σ bonds, we can multiply the number of σ bonds by 2: 12 σ bonds × 2 valence electrons per σ bond = 24 valence electrons used for σ bonds
04

(d) Valence electrons used to make π bonds

In benzaldehyde, we have the following π bonds: 1 π bond between oxygen and carbon 1 π bond between carbons in the phenyl ring Total π bonds: 1 + 1 = 2 π bond Every π bond uses 2 valence electrons, and hence to calculate the number of valence electrons used for π bonds, we can multiply the number of π bonds by 2: 2 π bonds × 2 valence electrons per π bond = 4 valence electrons used for π bonds
05

(e) Valence electrons remaining in nonbonding pairs

To find the number of valence electrons remaining in nonbonding pairs, we can subtract the valence electrons used for σ bonds and π bonds from the total valence electrons: Total valence electrons - valence electrons used for σ bonds - valence electrons used for π bonds = nonbonding pairs of valence electrons 40 - 24 - 4 = 12 valence electrons in nonbonding pairs

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