Textbook Question
Starting with formaldehyde and the alkyl halides shown as the only sources of carbon, provide a synthesis of the following alcohol.
609
views
12. Alcohols, Ethers, Epoxides and Thiols
Alcohol Synthesis
Struggling with Organic Chemistry?
Join thousands of students who trust us to help them ace their exams!Watch the first videoMultiple Choice
Which of the following is the best synthesis of the given molecule?
A
B
C
D
Verified step by step guidance1
Identify the target molecule: The target molecule is a secondary alcohol with a methoxy group and a tertiary butyl group.
Analyze the first reaction: Hydroboration-oxidation (BH3, NaOH, H2O2) adds water across a double bond in an anti-Markovnikov fashion, resulting in an alcohol at the less substituted carbon.
Analyze the second reaction: Oxymercuration-demercuration (Hg(OAc)2, NaBH4) adds water across a double bond in a Markovnikov fashion, resulting in an alcohol at the more substituted carbon.
Analyze the third reaction: Acid-catalyzed hydration (H2O, H2SO4) also adds water in a Markovnikov fashion, similar to oxymercuration-demercuration.
Analyze the fourth reaction: Radical addition of HBr (HBr, H2O2) adds HBr across a double bond in an anti-Markovnikov fashion, resulting in a bromide at the less substituted carbon, not an alcohol.
2:26mWatch next
Master Forming alcohols through Oxymercuration-Reduction. with a bite sized video explanation from Johnny
Start learningRelated Videos
Related Practice
Alcohol Synthesis practice set
Problem sets built by lead tutorsExpert video explanations