(a)
Interpretation:
A systematic scheme for the transformation of the cyclopentanecarboxylic acid from cyclopentanol is to be stated.
Concept introduction:
When an unsymmetrical 
, an alkyl bromide is formed. The substitution of in an alkene takes place by Markovnikov’s rule. According to Markovnikov’s rule, halide is substituted to the carbon atom which bears less number of hydrogen atoms and hydride ion is substituted to the carbon atom which bears more number of hydrogen atoms.
Grignard reagents are
(b)
Interpretation:
A systematic scheme for the transformation of the octanoic acid from 
is to be stated.
Concept introduction:
When an unsymmetrical alkene is reacted with , an alkyl bromide is formed. The substitution of in an alkene takes place by Markovnikov’s rule. According to Markovnikov’s rule, halide is substituted to the carbon atom which bears less number of hydrogen atoms and hydride ion is substituted to the carbon atom which bears more number of hydrogen atoms.
Grignard reagents are organometallic compounds which are prepared using alkyl halides in the presence of magnesium metal in dry ether. These reagents act as strong nucleophiles and bases.
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Chapter 20 Solutions
Organic Chemistry
- Starting with acid chloride with exactly 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules:arrow_forwardCompound A was oxidized with periodic acid to give B, which after acid hydrolysis gave C. Bromine oxidation of C gave D. Suggest structural formulas, including stereochemistry, for compounds B, C, and D.arrow_forwardSuggest with explanation on how you would prepare the compound, 4-chloroaniline from anilinearrow_forward
- Wolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.arrow_forwardSuggest reagents and reaction conditions for each of the following reactionsarrow_forwardCompound A produce compound D while undergo Friedel Crafts Alkylation. Compound D is then oxidized and produce compound E (C11H12O3) as a major product.What are the possible structural formula of compound D and E?arrow_forward
- Stearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?arrow_forwardGive the reagents and conditions necessary for the following conversion. A to B, B to D, B to C, B to E, E to F, E to G, G to H, H to I. Hence deduce the name and structural formula of the compounds C and I. Compare the procedure for converting F and E to G.arrow_forwardGive the structure of compound 1 and compound 2arrow_forward
- Compound A, C3H7Br, does not react with cold dilute potassium permanganate solution. Upon treatment with potassium hydroxide in ethanol, A gives only product B, C3H6. Unlike A, B decolourises potassium permanganate solution. Ozonolysis of Bgives C, C2H4O, and D, CH2O. Suggest the structural formulae of A, B, C and D.Write the equations for all the reactions involved.arrow_forwardSuggest reactivity of compound A, B and C in increasing order of E2 reactionarrow_forward3. Obtain acetophenone and acetaldehyde by reaction of glycols with periodic acid. Justify your answer with the reaction mechanism.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning