Exam 10: Structure and Synthesis of Alcohols

________ is the major intermolecular attraction responsible for the relatively high boiling points of alcohols.

Provide the reagents necessary to accomplish the following transformation. 2-methyl-2-octene to 2-methyloctan-3-ol

Provide the major organic product of the reaction below.

What gaseous byproduct is evolved when sodium metal is added to ethanol?

Provide an acceptable name for the compound below.

Provide the major organic product of the following reaction.

Given the set of reactants below, complete the acid-base reaction, and indicate whether the equilibrium favors reactants or products. CH₃O^- + HCl →

Using any compound that contains a carbonyl as your starting material, how would you synthesize 2-methylhexan-2-ol?

Explain why phenol is about 10⁶ times more acidic than methanol. Use appropriate resonance structures as part of your explanation.

2-Methylbutan-1-ol is classified as ________.

Which is more soluble in water, butan-1-ol or decan-1-ol? Explain briefly.

2-Methylpentan-3-ol is classified as ________.

Show how one might prepare 3-methylpentane by beginning with 2-iodobutane and using a Gilman reagent.

Provide the reagents necessary to carry out the multistep synthesis shown below.

Provide the major organic product of the reaction below.

Provide an acceptable name for the following compound.

Provide the reagents necessary to carry out the transformation shown below.

Identify the structure of the product of the following reaction.

Reaction of ethylmagnesium bromide with which of the following compounds yields a primary alcohol after quenching with aqueous acid?

How would one used a Gilman-based synthesis to accomplish the following transformation? pentanal (CH₃CH₂CH₂CH₂CHO) to heptan-3-ol