EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 16, Problem 16.58AP
Interpretation Introduction
Interpretation:
The structures of the compound
Concept introduction:
Number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton, less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.
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5) Compound A reacted with Mg in ether to give B. Compound B is with Ethyl bromide to give
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(a) Draw the structure of a compound of molecular formula C6H10 that reacts with H2 in the presence of Pd-C but does not react with H2 in the presence of Lindlar catalyst. (b) Draw the structure of a compound of molecular formula C6H10 that reacts with H2 when either catalyst is present.
Compound A (C6H12O2) reacts with water, acid, and heatto yield compound B (C5H10O2) and compound C (CH4O).Compound B is acidic. Deduce possible structures of compounds A, B, and C
Chapter 16 Solutions
EBK ORGANIC CHEMISTRY
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Prob. 16.3PCh. 16 - Prob. 16.4PCh. 16 - Prob. 16.5PCh. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - Prob. 16.9PCh. 16 - Prob. 16.10P
Ch. 16 - Prob. 16.11PCh. 16 - Prob. 16.12PCh. 16 - Prob. 16.13PCh. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Prob. 16.16PCh. 16 - Prob. 16.17PCh. 16 - Prob. 16.18PCh. 16 - Prob. 16.19PCh. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Prob. 16.22PCh. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Prob. 16.25PCh. 16 - Prob. 16.26PCh. 16 - Prob. 16.27PCh. 16 - Prob. 16.28PCh. 16 - Prob. 16.29PCh. 16 - Prob. 16.30PCh. 16 - Prob. 16.31PCh. 16 - Prob. 16.32PCh. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - Prob. 16.35APCh. 16 - Prob. 16.36APCh. 16 - Prob. 16.37APCh. 16 - Prob. 16.38APCh. 16 - Prob. 16.39APCh. 16 - Prob. 16.40APCh. 16 - Prob. 16.41APCh. 16 - Prob. 16.42APCh. 16 - Prob. 16.43APCh. 16 - Prob. 16.44APCh. 16 - Prob. 16.45APCh. 16 - Prob. 16.46APCh. 16 - Prob. 16.47APCh. 16 - Prob. 16.48APCh. 16 - Prob. 16.49APCh. 16 - Prob. 16.50APCh. 16 - Prob. 16.51APCh. 16 - Prob. 16.52APCh. 16 - Prob. 16.53APCh. 16 - Prob. 16.54APCh. 16 - Prob. 16.55APCh. 16 - Prob. 16.56APCh. 16 - Prob. 16.57APCh. 16 - Prob. 16.58APCh. 16 - Prob. 16.59APCh. 16 - Prob. 16.60APCh. 16 - Prob. 16.61APCh. 16 - Prob. 16.62APCh. 16 - Prob. 16.63APCh. 16 - Prob. 16.64APCh. 16 - Prob. 16.65APCh. 16 - Prob. 16.66APCh. 16 - Prob. 16.67APCh. 16 - Prob. 16.68AP
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- Compound A of molecular formula C8H₁4 is reduced by sodium in liquid ammonia to give compound of molecular formula C8H16. product (Y). Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5- dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H₁40 product, but reaction with bromine gives an achiral C8H₁4Br2 product. What are the identities of A and B? 14 A is 2,5-dimethyl-3-hexyne; B is cis-2,5-dimethyl-3-hexene A is 2,5-dimethyl-3-hexyne; B is trans-2,5-dimethyl-3-hexene A is 2,5-dimethyl-1,5-hexadiene; B is 2,5-dimethyl-3-hexyne A is 2,5-dimethyl-2,4-hexadiene; B is cis-2,5-dimethyl-3-hexenearrow_forward24.82 When the compound shown here is heated, ethene gas is evolved and a product with the formula C14H3O2 is formed. The 'H NMR and 13C NMR spectra of C14H8O2 are shown below. (There are two signals >150 ppm in the 13C NMR spectrum. Recall that the 13C NMR signal at 77 ppm is from the CDCI3 solvent.) (a) Draw the structure of C,14H3O2. (b) Draw the mechanism that accounts for its formation. (c) What is the main driving force that favors the products of this reaction? ? C14H3O2 C14H8O2 9. 8 7 6 4 3 2 1 250 200 150 100 50 Chemical shift (ppm) Chemical shift (ppm)arrow_forwardAn organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.arrow_forward
- Compound A of molecular formula C8H14 is reduced by sodium in liquid ammonia to give compound B of molecular formula C8H16. product (Y).Both A and B undergo hydrogenation in the presence of a platinum catalyst to give 2,5-dimethylhexane. Ozonolysis of B with an oxidative workup produces a carboxylic acid of molecular formula C4H8O2. Reaction of B with a peroxyacid gives a chiral C8H14O product, but reaction with bromine gives an achiral C8H14Br2 product. What are the identities of A and B?arrow_forwardCompound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD I) Draw the structural formula of compounds AA, BB, CC and DD. 2)Name the type of chemical reaction for the formation of compound CC.arrow_forwardAn unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.arrow_forward
- 1. (a) Describe aromaticity, Kekule structure and resonance structure for benzene. (b) Why is benzene more stable than aliphatic alkenes?arrow_forwardCompund ( A) C6H12 is treated with chlorine in the presence of carbon tetrachloride to given (B)C6H12Cl2.Compund (B) is treated with alcoholic KoH,followed by NaNH2 ,resulting in this formation of (C).compound (C) is treated with hydrogen in the presence of nickel catalysts to give 2methylpentane. Compound (C) does not react with sodamide or ammonical solution of silver nitrate .Ozonolysis of (A) give two aldehyde, (D) and (E) .Compound (E) is identified as acetaldehyde .From this information,describe the structural formula (A) ,(B) ,(C) And (C).write equation for all reactionarrow_forwardDraw the structure of a compound of molecular formula C6H10 that reacts with H2 in the presence of Pd-C but does not react with H2 in the presence of Lindlar catalyst.arrow_forward
- Compound A has molecular formula C7H15B.. Treatment of compound A with sodium ethoxide yields only one elimination product (compound B) and no substitution products. When compound B is treated with dilute sulfuric acid, compound C is obtained, which has molecular formula C7H160. Draw the structures of compounds A, B, and C.arrow_forwardWhen the reagent, Br2 in CCI4, (reddish-brown color), was added to Compound A of molecular formula C9H16, the reddish-brown color of the reagent changed to colorless, after the mixture was shaken. One mole of Compound A reacted with 1 mole of Hydrogen gas in the presence of Nickel catalyst to form a Compound B of molecular formula, C9H18. When the reagent, Br2 in CCI4, (reddish-brown color), was added to Compound B of molecular formula C9H18, the reddish-brown color of the reagent changed to colorless, after the mixture was shaken. Provide two possible structural formulas and corresponding IUPAC names of Compound A that will satisfy the above information. Provide a brief explanation for your answers:arrow_forwardCompound A (C5H8) readily reacts with bromine (Br2) at room temperature to discharge the purple colour of bromine and form Compound B (C5H8Br2). When Compound A is treated with H2 in the presence of a transition metal catalyst, it is converted to compound C (C5H10). When treated with HCl, compound A is converted to compound D (C5H9Cl). B, Cand D are saturated compounds. Given this information, propose structural formulas for compounds A, B, C, and D.arrow_forward
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