Let's solve each problem step-by-step: --- ## 1. Reduction of Cyclohexanecarboxaldehyde with LAH **Starting material:** Cyclohexanecarboxaldehyde (a cyclohexane ring with a CHO group) **Reagents:** 1. LAH (Lithium aluminum hydride) 2. H₂O **Step-by-step:** 1. **Reduction**: LAH is a strong reducing agent that reduces aldehydes to primary alcohols. 2. **Work-up**: Addition of water protonates the alkoxide intermediate to give the final alcohol. **Product:** Cyclohexanemethanol (a cyclohexane ring with a CH₂OH group) --- ## 2. Reaction of Cyclohexanecarboxaldehyde with Propylmagnesium Bromide (Grignard) **Starting material:** Cyclohexanecarboxaldehyde **Reagents:** 1. Propylmagnesium bromide (Grignard, C₃H₇MgBr) 2. H₂O (work-up) **Step-by-step:** 1. **Nucleophilic addition:** The propyl group from the Grignard adds to the carbonyl carbon, forming an alkoxide intermediate. 2. **Work-up:** Aqueous work-up protonates the alkoxide to give a secondary alcohol. **Product:** 1-propyl-1-hydroxycyclohexane (A cyclohexane ring with a CH(OH)-C₃H₇ group attached) --- ## 3. Reaction of Cyclohexanone with 2 Equiv. of Propylmagnesium Bromide **Starting material:** Cyclohexanone **Reagents:** 1. 2 eq. Propylmagnesium bromide 2. H₂O **Step-by-step:** 1. **First addition:** Propyl group from Grignard adds to the carbonyl carbon, forming a tertiary alkoxide. 2. **Second addition:** The second equivalent of Grignard can add to the carbonyl if it is present as an ester or acid chloride, but with a ketone, only one equivalent generally reacts (unless in excess or with esters). Here, "2 eq." ensures complete reaction. 3. **Work-up:** Alkoxide gets protonated to give a tertiary alcohol. **Product:** 1,1-dipropyl-1-hydroxycyclohexane (A cyclohexane ring with a C(OH)(C₃H₇)₂ group attached, both propyl groups attached to the same carbon as the OH) --- ## **Summary Table** | Problem | Reagents | Product Structure | |---------|---------------------------|----------------------------------------------------------| | 1 | 1. LAH, 2. H₂O |  | | 2 | 1. PrMgBr, 2. H₂O |  | | 3 | 1. 2 eq PrMgBr, 2. H₂O |  | *(Images are for illustrative purposes; the actual sketch should show the correct groups on the cyclohexane ring as described above.)* --- **Let me know if you'd like to see the mechanism for any of these steps!**