Use retrosynthetic analysis to suggest a way to synthesize 4-methyl-3-hexanol using the Grignard reaction (Click and drag the appropriate images to the reactant positions in the following reaction.) Н,о* ОН 4-methyl-3-hexanol CH3CHMgBr CH3 Н CH3CHCH2MgBr CH3CH2MgBr CH3 CH2Mg Br H -Mg Br CH3CH2CH2CH2Mg Br Н "Н

After each arrow fill in the major product of the reactions below. Assume that there is one molar equivalent of each of the reagents unless otherwise stated. ດ Hacoli OCH₂ H300 NaOCH 3 CH₂OH o 12/1 SOH 2) CH3CH2NH, HNOS 2504 00 い 十 Na bet EtOH NH (equivalent) weak base (Nazlos) я NaCN, HCL 1) LDA, -78°C 2)

The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. ОН ОН p-TSCI CH,COO Na+ A 1. LIAIH, pyridine DMSO 2. H,О (R)-2-Octanol (S)-2-Octanol Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.

Among the tertiary alcohols shown below, which one cannot be synthesized by reacting an appropriate Grignard reagent with an ester? CH2CH3 H3C-C-OH CH3 CH3 H3C-C-OH CH3 CH2CH3 H3C-C-OH CH2CH3 CH,CH3 H3C-C-OH CH(CH3)2 CH(CH3)2 H3C-C-OH CH(CH3)2