For each compound, predict the major product of free-radical bromination. Remember that bromination is highly selective, and only the most stable radical will be formed.
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Verified step by step guidance

1. Step 1: Analyze the structure of the compound provided. The compound is a bicyclic structure with two fused cyclohexane rings. Identify all the possible hydrogen atoms that can be abstracted to form radicals.
2. Step 2: Recall that bromination is highly selective and prefers the formation of the most stable radical. Stability of radicals follows the order: tertiary > secondary > primary > methyl. Look for tertiary carbons in the structure where a radical can form.
3. Step 3: Identify the positions where bromination can occur. In this case, the tertiary carbons in the bicyclic structure are the most likely sites for radical formation. These positions will lead to the major products.
4. Step 4: Consider the stereochemistry of the compound. Since the structure is bicyclic, bromination at different tertiary positions may lead to two distinct products due to the spatial arrangement of the molecule.
5. Step 5: Predict the major products by substituting bromine at the identified tertiary positions. Ensure that you account for the selectivity of bromination and the stability of the resulting radicals.

Key Concepts

Free-Radical Bromination

Free-radical bromination is a reaction where bromine (Br2) reacts with alkanes to form alkyl bromides through a radical mechanism. This process involves three main steps: initiation, propagation, and termination. The reaction begins with the homolytic cleavage of the Br-Br bond, generating bromine radicals that can abstract hydrogen atoms from alkanes, leading to the formation of more stable radicals.

Radical Stability

The stability of radicals is crucial in predicting the products of free-radical bromination. Radicals are more stable when they are tertiary (attached to three carbon atoms) compared to secondary or primary radicals. This stability influences which hydrogen atoms are abstracted during the reaction, as the formation of the most stable radical intermediate is favored, leading to the major product.

Selectivity in Bromination

Bromination is known for its selectivity, meaning it preferentially reacts with the most stable radical. This selectivity arises from the energy differences between the various radical intermediates formed during the reaction. As a result, the major product of bromination will be the one derived from the most stable radical, which is typically the one that forms from the most substituted carbon in the alkane.