12. Molecular Shapes & Valence Bond Theory

Hybridization

12. Molecular Shapes & Valence Bond Theory

Hybridization

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00:51

Hybridization Concept 1

Hybridization Concept 2

Hybridization Example 1

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Valence Bond Theory Explained (with examples, H2, CH4)

07:45

Valence Bond Theory Explained (with examples, H2, CH4)

Hybridization of Atomic Orbitals - Sigma & Pi Bonds - Sp Sp2 Sp3

The Organic Chemistry Tutor

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16:59

Valence Bond Theory & Hybrid Orbitals

Valence Bond Theory & Hybrid Atomic Orbitals

The Organic Chemistry Tutor

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10:52

Orbitals: Crash Course Chemistry #25

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Multiple Choice

How many of the following molecules have sp³d² hybridization on the central atom?

SeCl₆ XeCl₄ IF₅ AsCl₅

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Multiple Choice

How many unhybridized orbitals does the beryllium atom possess in BeCl₂?

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Open Question

Draw and determine the hybridization and unhybridized orbitals for the following covalent compound.

KrBr₄ Hybridization:

Unhybridized Orbitals:

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Multiple Choice

Determine the geometry around the central oxygen atom and the molecular polarity of dimethyl ether:

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Multiple Choice

What is the hybridization of the nitrogen atom in ammonia?

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Textbook Question

Which of the following molecules has a central atom with sp3 hybridization? (LO 8.4) (a) PCl5 (b) OF2 (c) CO2 (d) SF4

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Textbook Question

The orbital diagram that follows presents the final step in the formation of hybrid orbitals by a silicon atom. (b) What type of hybrid orbital is produced in this hybridization?

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Textbook Question

The connections between atoms in the amino acid histidine are shown. Complete the electron-dot structure by adding multiple bonds and lone pairs of electrons. Give the hybridization on the numbered carbon and nitrogen atoms. (LO 8.4)

(a) N1 = sp2, N2 = sp, C1 = sp2, C2 = sp3 (b) N1 = sp2, N2 = sp2, C1 = sp3, C2 = sp2 (c) N1 = sp3, N2 = sp, C1 = sp2, C2 = sp3 (d) N1 = sp3, N2 = sp2, C1 = sp2, C2 = sp3

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Textbook Question

In the hydrocarbon

(a) What is the hybridization at each carbon atom in the molecule?

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Textbook Question

Use the chemical structure for Tagamet, a drug used to treat peptic ulcers and heartburn, to answer questions 8 and 9.

Which orbitals overlap to form bond 1? (LO 8.5) (a) s bond: N 1sp22 with C 1sp22; p bond: N (p) with C (p) (b) N 1sp22 with C 1sp22 (c) s bond: N 1sp22 with C 1sp22; p bond: N 1sp22 with C 1sp22 (d) s bond: N (sp) with C 1sp22; p bond: N (p) with C (p)

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Textbook Question

The drawing below shows the overlap of two hybrid orbitals to form a bond in a hydrocarbon. (b) Which of the following could be the identity of the hydrocarbon: (i) CH4, (ii) C2H6, (iii) C2H4, or (iv) C2H2?

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Textbook Question

Use the chemical structure for Tagamet, a drug used to treat peptic ulcers and heartburn, to answer questions 8 and 9.

Which orbitals overlap to form bond 2? (LO 8.5) (a) C (sp) with C (sp) (b) C (sp) with C 1sp22 (c) C 1sp22 with C 1sp22 (d) C 1sp32 with C 1sp22

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Textbook Question

The molecule shown below is called furan. It is represented in typical shorthand way for organic molecules, with hydrogen atoms not shown, and each of the 4 vertices representing a carbon atom.

(e) The C¬C¬C bond angles in furan are much smaller than those in benzene. The likely reason is which of the following: (i) The hybridization of the carbon atoms in furan is different from that in benzene, (ii) Furan does not have another resonance structure equivalent to the one above, or (iii) The atoms in a five-membered ring are forced to adopt smaller angles than in a six-membered ring.

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Textbook Question

The VSEPR model is a simple predictive tool that is usually, but not always, correct. Take urea, for instance, a waste product excreted in animal urine:

What hybridization would you expect for the C and N atoms in urea according to the VSEPR model, and what approximate values would you expect for the various bond angles? What are the actual hybridizations and bond angles based on the molecular model shown? 1Red = O, gray = C, blue = N, ivory = H.2

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Textbook Question

For each statement, indicate whether it is true or false. (d) Nonbonding electron pairs cannot occupy a hybrid orbital.

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Textbook Question

Consider the molecule BF3. (c) What hybrid orbitals should be constructed on the B atom to make the B–F bonds in BF3?

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Textbook Question

Consider the SCl2 molecule.(d) What valence orbitals, if any, remain unhybridized on the S atom in SCl2?

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Textbook Question

Consider the SCl2 molecule. (c) What hybrid orbitals should be constructed on the S atom to make the S-Cl bonds in SCl2?

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Textbook Question

Indicate the hybridization of the central atom in (d) AlI3.

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Textbook Question

Indicate the hybridization of the central atom in (b) SeF6

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Textbook Question

What is the hybridization of the central atom in (a) PBr5?

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Textbook Question

What is the hybridization of the central atom in (d) NO2?

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Textbook Question

What is the hybridization of the central atom in (c) O3?

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Textbook Question

Shown here are three pairs of hybrid orbitals, with each set at a characteristic angle. For each pair, determine the type of hybridization, if any, that could lead to hybrid orbitals at the specified angle. (a)

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Textbook Question

The valence electron configurations of several atoms are shown here. How many bonds can each atom make without hybridization? c. F 2s22p5

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Textbook Question

The valence electron configurations of several atoms are shown here. How many bonds can each atom make without hybridization? b. P 3s23p3

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Textbook Question

The valence electron configurations of several atoms are shown here. How many bonds can each atom make without hybridization? a. Be 2s2

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Textbook Question

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Textbook Question

The valence electron configurations of several atoms are shown here. How many bonds can each atom make without hybridization? c. O 2s22p4

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Textbook Question

The valence electron configurations of several atoms are shown here. How many bonds can each atom make without hybridization? a. B 2s22p1

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Textbook Question

(d) Can two s orbitals combine to form a p bond? Explain.

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Textbook Question

Write orbital diagrams (boxes with arrows in them) to represent the electron configuration of carbon before and after sp3 hybridization.

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Textbook Question

(b) What is the hybridization of the carbon atoms in each molecule?

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Textbook Question

Write orbital diagrams (boxes with arrows in them) to represent the electron configurations of carbon before and after sp hybridization.

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Textbook Question

Which hybridization scheme allows the formation of at least one p bond? sp3, sp2, sp3d2

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Textbook Question

What hybridization do you expect for atoms that have the following numbers of charge clouds? (c) 4

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Textbook Question

Which hybridization scheme allows the central atom to form more than four bonds? sp3, sp3d, sp2

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Textbook Question

Benzaldehyde, C7H6O, is a fragrant substance responsible for the aroma of almonds. Its Lewis structure is

(a) What is the hybridization at each of the carbon atoms of the molecule?

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Textbook Question

What spatial arrangement of charge clouds corresponds to each of the following kinds of hybridization? (a) sp3

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Textbook Question

Consider the Lewis structure for acetic acid, which is known as vinegar:

(a) What are the approximate bond angles about each of the two carbon atoms, and what are the hybridizations of the orbitals on each of them?

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Textbook Question

Consider the Lewis structure for acetic acid, which is known as vinegar: (b) What are the hybridizations of the orbitals on the two oxygen atoms, and what are the approximate bond angles at the oxygen that is connected to carbon and hydrogen? What are the hybridizations of the orbitals on the two oxygen atoms?

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Textbook Question

Write a hybridization and bonding scheme for each molecule. Sketch the molecule, including overlapping orbitals, and label all bonds using the notation shown in Examples 10.6 and 10.7. c. OF2

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Textbook Question

Write a hybridization and bonding scheme for each molecule. Sketch the molecule, including overlapping orbitals, and label all bonds using the notation shown in Examples 10.6 and 10.7. b. NH3

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Textbook Question

Write a hybridization and bonding scheme for each molecule. Sketch the molecule, including overlapping orbitals, and label all bonds using the notation shown in Examples 10.6 and 10.7. a. CCl4

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Textbook Question

Write a hybridization and bonding scheme for each molecule or ion. Sketch the structure, including overlapping orbitals, and label all bonds using the notation shown in Examples 10.6 and 10.7. d. I3-

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Textbook Question

Write a hybridization and bonding scheme for each molecule or ion. Sketch the structure, including overlapping orbitals, and label all bonds using the notation shown in Examples 10.6 and 10.7. a. COCl2 (carbon is the central atom)

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Textbook Question

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Textbook Question

Describe the hybridization of the carbon atom in the poisonous gas phosgene, Cl2CO, and make a rough sketch of the molecule showing its hybrid orbitals and p bonds.

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Textbook Question

Write a hybridization and bonding scheme for each molecule that contains more than one interior atom. Indicate the hybridization about each interior atom. Sketch the structure, including overlapping orbitals, and label all bonds using the notation shown in Examples 10.6 and 10.7. c. C2H6 (skeletal structure H3CCH3)

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Textbook Question

Consider the structure of the amino acid alanine. Indicate the hybridization about each interior atom.

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Textbook Question

What hybridization do you expect for the atom that is underlined in each of the following species? (a) IO2-

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Textbook Question

Consider the structure of the amino acid aspartic acid. Indicate the hybridization about each interior atom.

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Textbook Question

What is the hybridization of the B and N atoms in borazine, what are the values of the B¬N¬B and N¬B¬N bond angles, and what is the overall shape of the molecule?

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Textbook Question

(a) If you combine two atomic orbitals on two different atoms to make a new orbital, is this a hybrid orbital or a molecular orbital?

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Textbook Question

Benzyne, C6H4, is a highly energetic and reactive molecule. What hybridization do you expect for the two triply bonded carbon atoms? What are the 'theoretical' values for the C¬C‚C bond angles? Why do you suppose benzyne is so reactive?

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Textbook Question

Aspirin has the following connections among atoms. Complete the electron-dot structure for aspirin, tell how many s bonds and how many p bonds the molecule contains, and tell the hybridization of each carbon atom.

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Textbook Question

Draw a picture that shows all three 2p orbitals on one atom and all three 2p orbitals on another atom. (b) How many p bonds can the two sets of 2p orbitals make with each other?

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Textbook Question

The odor of cinnamon oil is due to cinnamaldehyde, C9H8O. What is the hybridization of each carbon atom in cinnamaldehyde? How many s and how many p bonds does cinnamaldehyde have?

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Textbook Question

The following molecular model is a representation of caffeine. Identify the position(s) of multiple bonds in caffeine, and tell the hybridization of each carbon atom. 1Red = O, blue = N, gray = C, ivory = H.2

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Textbook Question

The genetic code is based on four different bases with the structures shown here. Assign a geometry and hybridization to each interior atom in these four bases. d. guanine

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Textbook Question

Although I3- is a known ion, F3- is not. (d) Yet another classmate says F3- does not exist because F is too small to make bonds to more than one atom. Is this classmate possibly correct?

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Textbook Question

Which of the following statements about hybrid orbitals is or are true? (i) After an atom undergoes sp hybridization, there is one unhybridized p orbital on the atom, (ii) Under sp2 hybridization, the large lobes point to the vertices of an equilateral triangle, and (iii) The angle between the large lobes of sp3 hybrids is 109.5°.

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Textbook Question

How many types of hybrid orbitals do we use to describe each molecule? b. C2H5NO (four C ¬ H bonds and one O ¬H bond)

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Textbook Question

How many types of hybrid orbitals do we use to describe each molecule? a. N2O5

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Textbook Question

Indicate which orbitals overlap to form the s bonds in each compound. a. BeBr2 b. HgCl2 c. ICN

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Textbook Question

Sodium azide is a shock-sensitive compound that releases N2 upon physical impact. The compound is used in automobile airbags. The azide ion is N3-. (b) State the hybridization of the central N atom in the azide ion.

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Textbook Question

Butadiene, C4H6, is a planar molecule that has the following carbon–carbon bond lengths:

(b) From left to right, what is the hybridization of each carbon atom in butadiene?

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Textbook Question

The structure of borazine, B3N3H6, is a six-membered ring of alternating B and N atoms. There is one H atom bonded to each B and to each N atom. The molecule is planar. (e) What are the hybridizations at the B and N atoms in the Lewis structures from parts (a) and (b)? Would you expect the molecule to be planar for both Lewis structures? Would you expect the molecule to be planar for both Lewis structures?

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Textbook Question

Azo dyes are organic dyes that are used for many applications, such as the coloring of fabrics. Many azo dyes are derivatives of the organic substance azobenzene, C12H10N2. A closely related substance is hydrazobenzene, C12H12N2. The Lewis structures of these two substances are

(Recall the shorthand notation used for benzene.) (b) How many unhybridized atomic orbitals are there on the N and the C atoms in each of the substances? How many unhybridized atomic orbitals are there on the N and the C atoms in hydrazobenzene?

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Textbook Question

In the cyanate ion, OCN-, carbon is the central atom. (d) Which hybrid orbitals are used by the C atom, and how many p bonds does the C atom form?

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Textbook Question

Cyclooctatetraene dianion, C8H8 2-, is an organic ion with the structure shown. Considering only the p bonds and not the s bonds, cyclooctatetraene dianion can be described by the following energy diagrams of its p molecular orbitals:

(a) What is the hybridization of the 8 carbon atoms?

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Textbook Question

Many primary amines, RNH2, where R is a carboncontaining fragment such as CH3, CH3CH2, and so on, undergo reactions where the transition state is tetrahedral. (a) Draw a hybrid orbital picture to visualize the bonding at the nitrogen in a primary amine (just use a C atom for 'R').

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Textbook Question

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Textbook Question

Although polyethylene can twist and turn in random ways, the most stable form is a linear one with the carbon backbone oriented as shown in the following figure:

The solid wedges in the figure indicate bonds from carbon that come out of the plane of the page; the dashed wedges indicate bonds that lie behind the plane of the page. (a) What is the hybridization of orbitals at each carbon atom? What angles do you expect between the bonds?

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Textbook Question

The equilibrium constant Kc for the gas-phase thermal decom-position of cyclopropane to propene is 1.0 * 105 at 500 K:

(e) Why is cyclopropane so reactive? (Hint: Consider the hybrid orbitals used by the C atoms.)

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Open Question

Consider the structure of the amino acid alanine. Indicate the hybridization about each interior atom.

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Open Question

What types of orbital overlap occur in cumulene?

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Open Question

What is the hybridization of the central atom of each of the following molecules?

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Open Question

Which of the following hybridization schemes allows the formation of at least one π bond?

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Open Question

For each molecule shown here, indicate the hybridization of the central atom.

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Open Question

What is the hybridization of the central atom in each of the following:

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Open Question

Label each carbon atom with the appropriate hybridization.

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Open Question

Which hybridization scheme allows the formation of at least one π bond?

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Open Question

Identify which types of orbitals overlap to form the bonds between the atoms in a benzene molecule.

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Open Question

By examining electron domain geometry, one can determine that the ammonia molecule (NH₃) has

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Open Question

Predict the molecular shape and the hybridization of the central atom for: AsCl₄^-1, SeO₄^-2, BiF₅^-2

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Open Question

Fluorine has 7 valence electrons. Which of the following is true of a fluorine molecule (F₂)?

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Open Question

Which hybrid orbitals overlap in the C-N bond in Co(NH₂)₂?

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Open Question

draw the lewis structure of azide (n₃⁻) and then determine the hybridization of the central atom.

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Open Question

Which of the molecules below will be polar? CS₂, BF₃, SO₂, CH₃Br

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Open Question

Molecule with 3 atoms bonded to a central atom with 2 unshared pairs of electrons, such as ClF₃.

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Open Question

Draw the lewis structure of azide (N₃^-) and then determine the hybridization of the central atom.

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Open Question

Draw the lewis structure of SCl₂ and then determine the hybridization of the central atom.

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Open Question

Judging by the electron domain geometry, which type of hybrid orbitals does this molecule have?

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Open Question

How many of the following molecules have sp² hybridization on the central atom? HCN SO₂ OCl₂ XeCl₂

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12. Molecular Shapes & Valence Bond Theory

Hybridization

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