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When a consumer purchases a tomato, smell is one of the
Chapter 12, Problem 12.37(choose chapter or problem)
When a consumer purchases a tomato, smell is one of the factors affecting selection. Researchers in Japan have thus analyzed the volatile components of tomatoes using a novel method. Among the complex mixture of 367 compounds detected were 3-methylbutanal and hexanal (J. Agric. Food Chem. 2002, 50, 34013404). Propose a single synthesis that produces an equimolar mixture of these two compounds (equal amounts of both products) starting with one 1, one 2, and one 3 alcohol, each with fewer than six carbons. (Note that the designations 1, 2, and 3 for alcohols are analogous to those of alkyl halides.) O H O H 3-Methylbutanal Hexanal
Questions & Answers
QUESTION:
When a consumer purchases a tomato, smell is one of the factors affecting selection. Researchers in Japan have thus analyzed the volatile components of tomatoes using a novel method. Among the complex mixture of 367 compounds detected were 3-methylbutanal and hexanal (J. Agric. Food Chem. 2002, 50, 34013404). Propose a single synthesis that produces an equimolar mixture of these two compounds (equal amounts of both products) starting with one 1, one 2, and one 3 alcohol, each with fewer than six carbons. (Note that the designations 1, 2, and 3 for alcohols are analogous to those of alkyl halides.) O H O H 3-Methylbutanal Hexanal
ANSWER:Problem 12.37When a consumer purchases a tomato, smell is one of the factors affecting selection.Researchers in Japan have thus analyzed the volatile components of tomatoes using a novelmethod. Among the complex mixture of 367 compounds detected were 3-methylbutanal andhexanal (J. Agric. Food Chem. 2002, 50, 34013404). Propose a single synthesis that producesan equimolar mixture of these two compounds (equal amounts of both products) starting withone 1, one 2, and one 3 alcohol, each with fewer than six carbons. (Note that the designations1, 2, and 3 for alcohols are analogous to those of alkyl halides.) Step-by-step solution Step 1 of 2Primary alcohol and tertiary alcohol convert to alkene in presence of strong acid and ethane toconvert addition of bromine to form 1,2-dibromoethane addition of alc KOH to forms acetyleneagain sodium amide in excess attack on acetylene followed by tertiary alcohol to change1-bromo-2-methylpropane from. This 1-bromo-2methylpropane is attack on sodium acetylide toproduce 4-methyl-1-pentyne.After than sodium amide in excess to form acetylide ion after attack the 1-bromo-pentane(presence in secondary alcohol) and remove NaBr to form 2-methyl-4-decyne.