7576 Organic Chemistry Practice Problems

Using IUPAC system, Name the following molecules

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Using IUPAC system, Name the following molecules

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Consider the following molecule:


Using Cahn, Engold, Prelog priority system, assign priorities to each group, and based on your
assignment, label the stereocenter R or S.

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How many stereocenters does the molecule have?

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How many stereocenters does the molecule have?

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Circle the chiral centers on the following molecule. Circle only 1-atom.


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Draw bond dipoles inside the boxes

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Fill in all the lone pairs on the “heteroatoms”

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Using the Cahn, Ingold, Prelog priority system, assign and label priorities of each group attached to the stereocenter (1 through 4) in the box next to each group. Based on your assignments, determine the absolute configuration as R or S (circle R or S for each)

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Using the Cahn, Ingold, Prelog priority system, assign and label priorities of each group attached to the stereocenter (1 through 4) in the box next to each group. Based on your assignments, determine the absolute configuration as R or S (circle R or S for each)

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Follow the directions for the molecule drawn below (18 pts):
a. There are many different configurational isomers of the trisubstited cyclohexane below. Draw the lowest energy configurational isomer in its lowest energy chair conformation
b. Draw the chair-flip conformer of your molecule from 4a.
c. Redraw your molecule from 4a as its line-angle formula (i.e. fill in the dotted lines as dashes and/or wedges.

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Using the IUPAC system, name the following molecules


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Using the IUPAC system, name the following molecules

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Using the IUPAC system, name the following molecule

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Consider the molecule drawn below. Draw the Newman projection where the halogens are anti.

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Consider the molecule drawn below. Draw the Newman projection where the halogens are eclipsed. 

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Consider the molecule drawn below. Draw the Newman projection of the molecule as drawn above, looking down the C2-C3 bond.

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How many stereocenters does the molecule have?



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Draw the bond dipole for each indicated bond inside the box:

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What is the hybridization of each atom indicated with an arrow?

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Fill in all missing lone pairs

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Hydrocarbon (A), C9H16, is chiral, possess a ring of five carbon atoms, contains four methyl groups, and absorbs one equivalent of H2 upon treatment with H2 over nickel catalyst to yield a racemic hydrocarbon, C9H18. When hydrocarbon (A) is treated with peracetic acid (CH3COOOH) and then with CH3MgBr, the major product (after exposure to dilute acid) is a teriary alcohol (B). (B) is not chiral. What is the structure of (A) and (B)?

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Provide a synthetic pathway:

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Synthesize alcohol (L) from organic starting materials of 6 carbons or less:

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Show how the following compound could be prepared in a two-step synthesis in which the first step involves a Diels-Alder reaction between an appropriate diene and dienophile.

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