CARBON Hybridized atomic orbitals. sp3 + sp3 + sp3 + sp3. sp2 + sp2 + sp2 + p

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Logan Willis
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YBRIDIZATI ybridization is the mixing together of "" (i.e., s-, p-) to form new, hybridized. These new, hybridized, overlap to form σ and π bonds.

For neutral (no formal charge),, and atoms, the following guidelines in the table below can be used to predict the hybridization of these atoms in organic molecules.

Each orbital is used to form a sigma bond (methane) Tetrahedral geometry(td) 109 bond angles Four σ bonds Three of carbon's four valence three new.

1 YBRIDIZATI ybridization is the mixing together of "" (i.e., s-, p-) to form new, hybridized. These new, hybridized, overlap to form σ and π bonds. arbon, oxygen and nitrogen valence hybridize to form, or. For neutral (no formal charge),, and atoms, the following guidelines in the table below can be used to predict the hybridization of these atoms in organic molecules. ARB ybridized All four of carbon's valence orbitals mix to energy) orbitals are generated after hybridization. Each orbital is used to form a sigma bond (methane) Tetrahedral geometry(td) 109 bond angles Four σ bonds Three of carbon's four valence three new. The unhbridized p-orbital is used for π Three new degenerate orbitals are formed after hybridization. The p orbital remains unhybridized. The orbitals are used to form σ bonds and the p orbital is used to form a π + + p + p (ethylene) Trigonal planar geometry Three σ bonds, one π bond Two of carbon's four valence two new. The unhbridized p-orbitals are used for π Two new degenerate orbitals are generated after hybridization. The two p orbitals remain unhybridized. The orbitals are used to form σ bonds and the p orbitals are used to form π bonds. (acetylene) Linear geometry Two σ bonds, two π bonds

ITRGE ybridized All four of nitrogen's valence orbitals mix to energy) orbitals form after hybridization.

(ammonia) Trigonal pyramidal Bond angles: 107 Three σ bonds and 1 lone pair Three of nitrogen's four box) to form three new hybridized orbitals.

Two of the orbitals are used to form σ bonds, one is used for a lone pair and the p orbital is used to form a π + + p + p (formaldamine) Bent geometry Two σ bonds, one

2 ITRGE ybridized All four of nitrogen's valence orbitals mix to energy) orbitals form after hybridization. Three of the orbitals are used to form σ bonds and one is used for a lone pair. (ammonia) Trigonal pyramidal Bond angles: 107 Three σ bonds and 1 lone pair Three of nitrogen's four box) to form three new hybridized orbitals. orbital is used for π Three new degenerate orbitals form after hybridization. The p orbital remains unhybridized. Two of the orbitals are used to form σ bonds, one is used for a lone pair and the p orbital is used to form a π + + p + p (formaldamine) Bent geometry Two σ bonds, one lone pair and one π bond Two of nitrogen's four valence two new. orbitals are used for π Two new degenerate orbitals are generated after hybridization. The two p orbitals remain unhybridized. ne of the orbitals is used to form a σ bond and the other is used for the lone pair. The two unhybridized p orbitals are used to form two π bonds. (acetonitrile) Linear geometry ne σ bond, one lone pair and two π bonds

(dimethylether) Bent 104 bond angles Two σ bonds and 2 lone pairs Three of oxygen's four valence three new.

3 XYGE ybridized All four of oxygen's valence orbitals mix to Four new orbitals form after hybridization. Two of the orbitals are used to form σ bonds and two are used for two lone pairs. (dimethylether) Bent 104 bond angles Two σ bonds and 2 lone pairs Three of oxygen's four valence three new. orbital is used for π Three new orbitals form after hybridization. The p orbital remains unhybridized. ne of the orbitals are used to form σ bond, two are used for lone pairs and the p orbital is used to form a π (formaldehyde) Linear geometry Two σ bonds, one lone pair and one π bond Example molecules: 3 3 3

For charged atoms (those with formal charge), patterns for ecifically hybridized atoms is different. harged atoms are encountered during chemical reactions as reaction intermediates.

ne of the p orbitals remains unhybridized Three new, orbitals are formed after hybridization. The three orbitals are used to form σ bonds.

4 For charged atoms (those with formal charge), patterns for ecifically hybridized atoms is different. harged atoms are encountered during chemical reactions as reaction intermediates. ARGED ARB ATMS ybridized Bonding Pattern, geometry and bond angles carbocation 1s 2 2s 2 2p 1 Three of carbon's valence orbitals mix to form three new. ne of the p orbitals remains unhybridized Three new, orbitals are formed after hybridization. The three orbitals are used to form σ bonds. The p orbital remains vacant (no electrons and is available to accept electrons from a nucleophile.) Trigonal planar Three σ bonds and 1 vacant p-orbital carbanion 1s 2 2s 2 2p 3 All four of carbon's four form four new. Four new degenerate orbitals form after hybridization. Three of the orbitals are used to form σ bonds, one is used for a lone pair. Trigonal pyramidal 107 bond angles Three σ bonds and one lone pair

ARGED ITRGE ATMS itrogen atoms may take on a positive charge or a negative charge in a reactive state.

egatively charged nitrogen atoms are much less common but may be generated during chemical reactions. ybridized All four of nitrogen's energy) orbitals form after hybridization.

Two the orbitals are used to form σ bonds and two are used for two lone pairs. Bent geometry 104 bond angles Two σ bonds ; 2 lone pairs Three of nitrogen's four box) to form three new.

5 ARGED ITRGE ATMS itrogen atoms may take on a positive charge or a negative charge in a reactive state. Positively charged atoms are most commonly encountered when the nitrogen atom uses its lone pair to accept a proton () in an acid-base reaction. egatively charged nitrogen atoms are much less common but may be generated during chemical reactions. ybridized All four of nitrogen's energy) orbitals form after hybridization. All four of the orbitals are used to form σ bonds. Tetrahedral Bond angles: 109 Four σ bonds All four of nitrogen's energy) orbitals form after hybridization. Two the orbitals are used to form σ bonds and two are used for two lone pairs. Bent geometry 104 bond angles Two σ bonds ; 2 lone pairs Three of nitrogen's four box) to form three new. orbital is used for π Three new degenerate orbitals form after hybridization. The p orbital is unhybridized. Three of the orbitals are used to form σ bonds, and the p orbital is used to form a π Trigonal planar Three σ bonds; one π bond Two of nitrogen's four box) to form two new. orbitals are used for π + + p + p Two new degenerate orbitals are generated after hybridization. The two p orbitals remain unhybridized. The orbitals are used to form σ bonds. The two unhybridized p orbitals are used to form two π bonds. Linear Two σ bonds; two π bonds

ARGED XYGE ATMS xygen atoms may take on a positive charge or a negative charge in a reactive state.

egatively charged oxygen atoms (hydroxides or alkoxides) are formed under basic conditions. ybridized All four of oxygen's Four new, orbitals form after hybridization.

Three of the orbitals are used for lone pairs and one for a σ ne σ bond ; 3 lone pairs Three of oxygen's four box) to form three new. orbital is used for π Three new orbitals form after hybridization.

6 ARGED XYGE ATMS xygen atoms may take on a positive charge or a negative charge in a reactive state. Positively charged atoms (oxonium ion) are most commonly encountered when the oxygen atom uses one of its lone pairs to accept a proton () in an acid-catalyzed reaction. egatively charged oxygen atoms (hydroxides or alkoxides) are formed under basic conditions. ybridized All four of oxygen's Four new, orbitals form after hybridization. Three of the orbitals are used for σ bonds and one for a lone pair Trigonal pyramidal Bond angles: 107 Three σ bonds; one lone pair All four of oxygen's Four new, orbitals form after hybridization. Three of the orbitals are used for lone pairs and one for a σ ne σ bond ; 3 lone pairs Three of oxygen's four box) to form three new. orbital is used for π Three new orbitals form after hybridization. The p orbital is unhybridized. Two of the orbitals are used to form σ bonds, one is for a lone pair and the p orbital for a π Bent Two σ bonds; one lone pair; one π bond Two of oxygen's four box) to form two new. orbitals are used for π + + p + p Two new orbitals are generated after hybridization. The two p orbitals remain unhybridized. The orbitals are used for one σ bond and one lone pair. The two unhybridized p orbitals are used to form two π bonds. Linear ne σ bonds; one lone pair; two π bonds

Chemistry 105, Chapter 7 Exercises

Chemistry 105, Chapter 7 Exercises hemistry 15, hapter 7 Exercises Types of Bonds 1. Using the periodic table classify the bonds in the following compounds as ionic or covalent. If covalent, classify the bond as polar or not. Mg2 4 i2 a(3)2