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Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Non è quello che usi tu?Cambia libro di testo
Capitolo 9, Problema 41c

Beginning with the molecules on the left of each chemical equation, synthesize the molecules shown. While there can be multiple ways of doing each synthesis, the minimum number of steps necessary is indicated over each reaction arrow.
(c)

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Step 1: Perform an elimination reaction on the starting molecule (cyclopentylmethyl bromide) to form an alkene. Use a strong base, such as potassium tert-butoxide, to remove the bromine atom and generate cyclopentylmethyl alkene (CH2=CH-cyclopentane).
Step 2: Carry out an ozonolysis reaction on the alkene formed in Step 1. Use ozone (O3) followed by a reducing agent like dimethyl sulfide (DMS) or zinc in acetic acid to cleave the double bond and form two products: formaldehyde (H2C=O) and cyclopentylacetaldehyde.
Step 3: Oxidize the aldehyde group in cyclopentylacetaldehyde to a ketone. Use a mild oxidizing agent such as PCC (pyridinium chlorochromate) or a stronger oxidizing agent like Jones reagent (CrO3/H2SO4) to convert the aldehyde to cyclopentylacetone.

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