12. Alcohols, Ethers, Epoxides and Thiols

(•) The following molecules were named incorrectly according to IUPAC nomenclature. Give the correct name of these compounds.

(a) 3-oxo-5-methylhexan-2-ol

(••) Using IUPAC rules, name the following molecules.

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(••) Draw the correct structure from the following IUPAC names:

(a) (4R,2Z)-4-methylhex-2-en-1-ol

(••) Draw the correct structure from the following IUPAC names:

(c) (1S,4R)-4-bromocyclohex-2-en-1-ol

Draw a condensed structure for each of the following:

g. 1-bromo-1-pentyne

h. 5-methyl-2-cyclohexenol

Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary.

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(g) <IMAGE>

Give a systematic (IUPAC) name for each diol

(a) CH3CH(OH)(CH2)4CH(OH)C(CH3)3

(b) HO-(CH2)8-OH

(c) <IMAGE>

Predict which member of each group is most soluble in water, and explain the reasons for your predictions.

(a) butan-1-ol, pentan-1-ol, or propan-2-ol

Give a systematic (IUPAC) name for each diol

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(e) <IMAGE>

Which of the following bases would favorably deprotonate a hydroxyl group?

(d) Et₃N

Which of the following bases would favorably deprotonate a hydroxyl group?

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