From the choices provided below, list the reagent(s) in order that will react with cis-3-hexene to form meso-3,4-hexanediol. List your answer as a single letter (single-step transformation) or a series of letters (multi-step transformation) with no commas separating them. For example, "hg" corresponds to: PCC NaOH NOTE: The order you in which you list your letters matters! Reagents: CL2/H2O RCO3H K2Cr2O7, H2SO4, H2O. heat SOCI2, pyridine NaNH2 (3 equivalents) OSO4, H2O2 NaOH pyridinium chlorochromate (PCC).

For cyclohexane compounds drawn in a chair conformation:   -axial bonds are vertical  -equatorial bonds are parallel to two bonds within the ring.  thus, as i assume the chair conformation is drawn:   -the x group is in an axial position, as are the five other vertical bonds.  -three axial bonds are on the top face of the ring  -the other three axial bonds are on the bottom face  the position of the second substituent on each ring carbon is equatorial.  gauche groups must be on an adjacent carbon such as carbon 6 and carbon 2, and also gauche groups are rotated by 60 degrees relative to each other.  drawing the newman projections for c1–c2 and c1–c6 aids in visualizing the groups that are gauche to the y group on c1.  click this link and watch some academic videos that may you more understand the topic