Alcohol Nomenclature - Online Tutor, Practice Problems & Exam Prep

Evaluate whether the base LiCN (pK_a of H—CN = 9.22) can favorably deprotonate a hydroxyl group (pK_a 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

Determine which alcohol in the given pair is more acidic. Explain your choice.

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

Determine which alcohol in the given pair is more acidic. Give an explanation for your choice.

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-ol
b. 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

Use IUPAC rules and write the molecule name for the given structure.

The given name is wrong, based on IUPAC rules. Provide the correct name of the compound below.

3,5-dimethyl-4-oxoheptan-2-ol

Draw the correct structure of (R, E)-5-methylhex-3-en-2-ol.

What is the structure of the molecule with an IUPAC name (1R,4S)-4-chlorocyclopent-2-en-1-ol?

What is the condensed structure of the given compounds?

i. 1-chloro-4-methylpent-1-yne

ii. 2,3-dimethylcyclopentan-1-ol

Determine the IUPAC name of the following alcohols and classify them as either primary (1°), secondary (2°), or tertiary alcohol (3°).

Predict which member is the least soluble in water: pentan-2-ol, butan-2-ol, or heptan-1-ol. Explain.

What are the IUPAC names of the diols given below?

(i) CH₃CH₂CH(OH)(CH₂)₃CH(OH)C(CH₃)₃

(ii) HO-(CH₂)₆-OH

(iii)

What are the systematic names of the following stereoisomers? (use cis/trans designation)

Can (CH₃)₃N favorably deprotonate an alcohol?

Note: The conjugate acid of (CH₃)₃N has a pK_a of 9.80

Determine if the given base can deprotonate the hydroxyl group in an alcohol.

Suggest plausible mechanisms for proton exchanges between methanol molecules under the following conditions:

(i) acidic condition.

(ii) basic condition.