Ch. 1 - A Review of General ChemistryWorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Hybridization describes orbitals, but molecular geometry describes the shape of the atom. 

Concept #1: Molecular Geometry Explained.

Note: Many professors refer to ALL sp2 hybridized atoms as “trigonal planar” even though that is technically not correct for atoms with lone pairs. Just go with the flow if that happens!

Let's find the hybridization and geometry of the indicated atoms in the following molecules:

Example #1: Predict the hybridization and molecular geometry of the following selected atoms.

Practice: Determine the hybridization of the following selected atoms: 

Practice: PRACTICE: Determine the hybridization and molecular geometry of the following selected atoms:

Additional Problems
For each molecule below, fill in the table to determine the electron geometry & molecular geometry about the CENTRAL ATOM. Then sketch a perspective drawing of the substance and LABEL ALL BOND ANGLES.  1. HCN      2. NO2-      3. NF3
VSEPR theory predicts an identical shape for all of the following, except: (hint: draw the Lewis structures before deciding ) a. OCl3+ b. Br2CO c. CH3● d. Et2O e. All have the same geometry f. none of the above
Predict the geometry of each atom except hydrogen in the compounds below: 
Predict the geometry of each atom except hydrogen in the compounds below: 
Predict the geometry of each atom except hydrogen in the compounds below: 
Predict the geometry of each atom except hydrogen in the compounds below: 
Draw a Lewis structure of the anion AlBr4- and determine its geometry. 
What is the hybridization of each carbon in CH 3CH=CHC≡CH?  What are the CCC bond angles?   
Predict the bond angles for all bonds in the following compounds:  (b)CH2O 
Predict the bond angles for all bonds in the following compounds:  (c)C2H4 
Predict the bond angles for all bonds in the following compounds:  (d)C2H2 
Predict the bond angles for all bonds in the following compounds:  (e) CH3OCH3 
Predict the bond angles for all bonds in the following compounds:  (f) CH3NH2 
Predict the bond angles for all bonds in the following compounds:  (h)CH3CN 
Identify the expected hybridization state and geometry for the central atom in each of the following compounds: 
Of the overlaps between an  s and a p orbital as shown in the illustration, one is bonding, one is antibonding, and the third is nonbonding (neither bonding nor antibonding). Which orbital overlap corresponds to which interaction? Why? 
Identify the hybridization state and geometry of each carbon atom in the following compounds: 
Identify the hybridization state and geometry of each carbon atom in the following compounds: 
Identify the hybridization state and geometry of each carbon atom in the following compounds: 
Consider the three compounds shown below and then answer the questions that follow:  (b) Which compound contains a nitrogen atom with trigonal pyramidal geometry? 
Consider the three compounds shown below and then answer the questions that follow:  (f) Which compound contains an sp2-hybridized carbon atom?
Consider the three compounds shown below and then answer the questions that follow:  (g) Which compound contains only sp3-hybridized atoms (in addition to hydrogen atoms)?   
Propose at least two different structures for a compound with six carbon atoms that exhibits the following features: (a) All six carbon atoms are sp2 hybridized.  
Propose at least two different structures for a compound with six carbon atoms that exhibits the following features: (c) There is a ring, and all of the carbon atoms are sp3 hybridized.
Propose at least two different structures for a compound with six carbon atoms that exhibits the following features: (d) All six carbon atoms are sp hybridized, and the compound contains no hydrogen atoms (remember that a triple bond is linear and therefore cannot be incorporated into a ring of six carbon atoms). 
A compound with molecular formula C5H11N has no π bonds. Every carbon atom is connected to exactly two hydrogen atoms. Determine the structure of the compound.   
Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the preparation of numerous new compounds and natural products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful procedure for temporarily hiding the reactivity of an isonitrile (Tetrahedron Lett. 2012, 53, 4536–4537).  (a) Identify the hybridization state for each highlighted atom in A.   
Isonitriles (A) are an important class of compounds because of the versatile reactivity of the functional group, enabling the preparation of numerous new compounds and natural products. Isonitriles can be converted to isonitrile dihalides (B), which represents a useful procedure for temporarily hiding the reactivity of an isonitrile (Tetrahedron Lett. 2012, 53, 4536–4537).  (d) Identify the hybridization state for each highlighted atom in B.
In Section 1.12 we discussed the effect that branching can have on the boiling point of a compound. In certain instances, branching may also affect how a molecule can react with different molecules. We use the term “steric hindrance” to describe how branching can influence reactivity. For example, greater “steric crowding” may decrease the reactivity of a C=C π bond (Org. Lett. 1999, 1, 1123–1125). In the following molecule, identify each π bond and determine which has a greater degree of steric crowding. (Note: This is not the same as “steric number”.)   
Ramelteon is a hypnotic agent used in the treatment of insomnia:  (g)  Identify the geometry of each atom (except for hydrogen atoms). 
Cycloserine is an antibiotic isolated from the microbe Streptomyces orchidaceous. It is used in conjunction with other drugs for the treatment of tuberculosis.  (g)  Identify the geometry of each atom (except for hydrogen atoms). 
Melatonin is an animal hormone believed to have a role in regulating the sleep cycle:  The structure of melatonin incorporates two nitrogen atoms. What are the hybridization state and geometry of each nitrogen atom? Explain your answer. 
What can be said about the stability of the molecule cyclopentyne? Would it be stable? Draw it and explain why or why not.
What is the hybridization and geometry of the indicated atom in the following molecule?
What is the hybridization and geometry of the indicated atom in the following molecule?
What is the hybridization and geometry of the indicated atom in the following molecule?
What is the hybridization and geometry of the indicated atom in the following molecule?
What is the hybridization and geometry of the indicated atom in the following molecule?
How many unhybridized p orbitals does an sp3 hybridized carbon have? What other types of orbitals are available for bonding? What are the bond angles?
What is the hybridization of a methyl radical? In which orbital does the unpaired electron reside in? What are the bond angles and geometry?
Predict the hybridization and geometry around each indicated atom.
I. Use VSEPR to determine the hybridization state of the indicated atom in the following moleculesII. In which type of orbital is the lone pair in the following carbanion?
Predict the approximate bond angles in the following molecule.
Place the following molecules in order of decreasing bond angle: NH3, CO2, CCl4, OF2
Use VSEPR to deduce the hybridization and molecular geometry of the ionized atoms in the following structures:
Consider a chemical species like the one in the previous problem in which a carbon atom forms three single bonds to three hydrogen atoms, but in which the carbon atom possesses an unshared electron pair.(a) What formal charge would the carbon atom have? (b) What total charge would the species have?(c) What total charge would the species have?(d) What would you expect the hybridization state of the carbon atom to be?
Use VSEPR theory to deduce the hybridization state of the negatively charged carbon in the following cumulene derived carbanion. In which orbital does the electron pair reside in? What is its geometry?
Label the molecular shape around each of the central atoms in the amino acid glycine.
If the analysis of carbon in a molecule indicates sp hybridization, what must be the shape around the carbon? a. Trigonal planar b. Linear c. Tetrahedral d. Cannot be determined
Why the following compound is not stable? (i) because the bond angles at the triple-bonded carbons, when the bonding orbitals overlap maximally, are 120° and therefore the sp-hybridized carbons can not simultaneously bind atoms other than hydrogen on both sides of triple-bond.(ii) because the bond angles at the triple-bonded carbons, when the bonding orbitals overlap maximally, are 180° and 180 degree angle cannot fit into the ring structure of such a size. (iii) because the bond angles at the triple-bonded carbons, when the bonding orbitals overlap maximally, are 180° and therefore the sp-hybridized carbons can not simultaneously bind atoms other than hydrogen on both sides of triple-bond.(iv) because the bond angles at the triple-bonded carbons, when the bonding orbitals overlap maximally, are 120° and 120° angle cannot fit into the ring structure of such a size.
Nicotine is an addictive substance found in tobacco. Identify the hybridization state and geometry of each of the nitrogen atoms in nicotine: Use the following values to indicate hybridization state: 1 = sp; 2 = sp2; 3 = sp3. Nitrogen 1 is ________ hybridized and  ________. Nitrogen 2 is _________ hybridized and  ________.
What is the molecular geometry around the methyl carbons (CH3) atom in the drawing below? (A) Linear (B) Bent (C) Trigonal planar (D) Trigonal pyramidal (E) Tetrahedral
Based on the structure below, what is the value for the H-N-CH3 bond angle? 
What is the molecular geometry about NA the molecule below? a. Linear b. Bent c. Trigonal planar d. Trigonal pyramidal e. Tetrahedral
The F - •S - F bond angles in SF6 are a. 90° and 120°b. 90° and 180°c. 109.5°d. 180°e. 120°
For question below use the Lewis structure for acetic acid shown here. The ideal value for the H-C-H bond angle about atom 1 is: a. 120° b. 60°c. 109.5°d. 90°e. 180°