Organic Chemistry
Evaluate whether the base LiCN (pKa of H—CN = 9.22) can favorably deprotonate a hydroxyl group (pKa of R—OH = 16.0).
Can the hydroxyl group of propan-2-ol be favorably deprotonated by the base potassium ethanolate?
Determine which alcohol in the given pair is more acidic. Explain your choice.
1-butanol and 2-chloro-1-butanol
2-propanol and 2-propanethiol
Determine which alcohol in the given pair is more acidic. Give an explanation for your choice.
2-fluoropropanol or 3-fluoropropanol
2-bromoethanol or 2-chloroethanol
Write IUPAC (systematic) names for the following alcohols:
Include stereochemistry if applicable.
Draw chemical structures corresponding to the following IUPAC names:
a. (S)-4-chloropent-4-en-2-olb. cis-cyclobutan-1,2-diol
For each pair of compounds, determine which of the two compounds has a higher water solubility. Give a brief explanation for your choice.(i) pentan-1-ol or cyclopentanol(ii) hexan-1-ol or phenol(iii) 3-ethylpentan-3-ol or heptan-2-ol(iv) pentan-2-ol or cyclopentane-1,3-diol(v)
For each pair of compounds, determine which compound boils at a higher temperature. Give a brief explanation for your predictions.(i) heptan-1-ol or 3,3-dimethylpentan-1-ol(ii) pentan-2-one or pentan-2-ol
