Show reagents to convert bromocyclopentane to each of the following compounds. Br OH OH (c) ОН (f) C=CH (b) Br OH (a) (d) (i) OMe OH OH "OMe (k) HO H `H.
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- Propose a plausible mechanism for the 1 to 2 conversion as shown, and explain the stereochemical result:-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.(R)-Pulegone, readily available from pennyroyal oil, is an important enantiopure building block for organic syntheses. Propose a mechanism for each step in this transformation of pulegone.
- Treatment of compound A (C8H17Br) with NaOCH2CH3 affords two constitutional isomers B and C. Ozonolysis of B affords CH2=O and (CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 and CH3CH2CHO. What is the structure of A?When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be C5H10O. Propose a likely structure for this product, suggesting a reasonable mechanistic pathway for its formationConsider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Deduce the mechanism of this reaction working step by step. Write all possible products showing the stereochemistry.
- Arrange the following compounds in their ease of undergoing an SN2 reaction: a. CH3CH2CH2-Cl b. (CH3)2CH-Br c. (CH3)3C-Cl d. CH3-BrWhich stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?What would be the expected major product or products when 1-ethylcyclohexene is treated with ozone (O3) followed by DMS?
- Compound X, C7H15Cl, is a chiral product of the radical chlorination of 2-methylhexane.Base-promoted E2 elimination of X gives a single product.What is the structure of X?When sodium methoxide base and hydrogen bromide are removed from trans-1-bromo 2-methyl cyclohexane, considering the conformation of the starting compound, find the product that will be formed by writing and explaining the mechanism of the reaction.Treatment of compound A (C8H17Br) with NaOCH2CH3 affords twoconstitutional isomers B and C. Ozonolysis of B affords CH2=O and(CH3CH2CH2)2C=O. Ozonolysis of C affords CH3CH2CH2COCH3 andCH3CH2CHO. What is the structure of A?