Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default.
(E)-1,2-dibromo-3-isopropyl-2-hexene Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default.
The Correct Answer and Explanation is:
Correct Answer:
To draw (E)-1,2-dibromo-3-isopropyl-2-hexene, follow these steps using your molecular drawing tool (like ChemDraw or MarvinSketch), using the Tools, Atoms, and Advanced Template toolbars:
Step-by-Step Drawing Instructions:
- Draw the Carbon Backbone (Hexene):
- Start by creating a 6-carbon straight chain (hexane).
- Add a double bond between carbon 2 and carbon 3 (→ this makes it 2-hexene).
- Add Substituents:
- Place a bromine (Br) atom on carbon 1.
- Place another Br atom on carbon 2.
- Place an isopropyl group (–CH(CH₃)₂) on carbon 3.
- Assign (E)-configuration:
- On the double bond at C2=C3, you have:
- On C2: Br (high priority) and C1 (chain).
- On C3: isopropyl (high priority) and C4 (chain).
- The (E)-configuration means the higher priority groups (Br and isopropyl) must be on opposite sides of the double bond.
- On the double bond at C2=C3, you have:
So, when drawing the molecule, make sure:
- The Br on carbon 2 is on one side of the double bond.
- The isopropyl group on carbon 3 is on the opposite side.
Explanation
(E)-1,2-dibromo-3-isopropyl-2-hexene is a substituted alkene, and understanding its structure requires knowledge of IUPAC nomenclature, stereochemistry (E/Z), and functional groups.
- Parent Chain and Numbering:
- The longest continuous chain with the double bond has six carbon atoms, hence hexene.
- The double bond begins at carbon 2, so we name it 2-hexene.
- The chain is numbered from the end closest to the double bond, ensuring substituents have the lowest possible numbers.
- Substituents:
- Two bromine atoms are attached to carbon atoms 1 and 2: thus, 1,2-dibromo.
- An isopropyl group (–CH(CH₃)₂) is attached to carbon 3: hence, 3-isopropyl.
- Stereochemistry – E/Z Notation:
- The double bond between C2 and C3 allows for cis-trans (E/Z) isomerism.
- To determine (E) or (Z), we apply the Cahn-Ingold-Prelog priority rules:
- On C2: Br > C1
- On C3: isopropyl > C4
- The (E)-isomer has the higher-priority groups on opposite sides of the double bond.
This molecule’s accurate drawing requires careful placement of atoms and substituents to reflect the correct connectivity and 3D arrangement, particularly for the (E)-stereochemistry, which impacts physical and chemical properties significantly.
