Reaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J 15). What is its structure? (Don't forget stereochemistry!). When this compound reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J1.9, 17.7), 3.25 (dd, J 10.0, 17.7), and 4.38 (1H, dd, J1.9, 10.0). Suggest a structure, assign the spectrum, and give a mechanism for the formation of B.

Reaction between this aldehyde and ketone in base gives a compound A with the proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J 15). What is its structure? (Don't forget stereochemistry!). When this compound reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13 (9H, s), 2.71 (1H, dd, J1.9, 17.7), 3.25 (dd, J 10.0, 17.7), and 4.38 (1H, dd, J1.9, 10.0). Suggest a structure, assign the spectrum, and give a mechanism for the formation of B.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Related questions

Q: Using proton NMR spectra, how could a chemist distinguish between the following two compounds? H. H.…

Q: 1H NMR signal assignment of ethyl 4-chlorocinnamate, label the proton environments according to the…

A: 1H-NMR spectroscopy is mainly used for the identification of the complete structure of an organic…

Q: Grinard Reaction with Aldehyde: (a) What peaks in the NMR spectrum most clearly demonstrate the…

A: Peak for CHO at ~9 ppm is the characteristic peak for aldehyde Labile proton in aliphatic region…

Q: 2. The following synthesis was planned. The 'H NMR spectrum of the final product was run and is…

A: In the first step, diazotization occurs to produce diazonium salt followed by the ring opening of…

Q: Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.

A: Nuclear magnetic resonance (NMR) is used for identifying the molecular structures, physical and…

Q: Addition of mesitylene to the strongly acidic solvent HF / SbF5 at -45 °C gives a new species which…

A: A question based on NMR spectroscopy. A chemical reaction at low temperature is given using the hint…

Q: 3. List the following compounds in order of reactivity towards MeOH (1 = highest, 4 = lowest) and…

A: The given reactants are tertiary halide.Also the nucleophile is weak.So it follows SN1 nucleophilic…

Q: H2SO4 НаО еxcces 'H NMR of B 6 H 3 H 1H (broad) 2 H lle PPM LOD IR of A D 4000 3000 2000 1S00 1000…

A: The correct answer is given below

Q: 7. Propose structures for compounds that fir the following ¹H NMR data: C4H6Cl₂ 2.18 8 (3H, singlet)…

A: 7) 1HNMR spectroscopy is used to determine the arrangement of Hydrogen atoms in the molecule.…

Q: A student mixes benzaldehyde with an unknown symmetrical ketone, compound C, in an aqueous sodium…

A: The question is based on the concept of spectroscopy. We have to identify the structure of C &D.

Q: Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in…

A: a). Structure of A: The lack of IR absorption suggests the absence of CO bond and NH bond or OH…

Q: Reaction of unknown A with HCl forms chlorohydrin B as the major product. A shows no absorptions in…

A: In order to determine the compound structure, IR spectrum and proton-NMR spectrum are utilized. The…

Q: C6H100, IR (cm-1): 2110, 3300 cm1 (sharp), 1H NMR (8): 3.31 (3H, s); 2.41 (1H, s), 1.43 (6H, s) H- I…

Q: Which compound is best represented by the 1H NMR spectra shown here? 1.06 ррm (d), 12

A: It explains the nature of protons (H) in unknown compound All magnetically equivalent protons gives…

Q: Propose a structure that is consistent with each set of 1H-NMR data. a) C5H10O 13C –NMR shows 4…

Q: Following are 'H-NMR and BC-NMR spectral data for compound G (CH0). From this information, deduce…

A: Calculation of double bond equivalence: DBE=C+1-H2-X2+N2=10+1-102=6 Thus the given compound must…

Q: O 1) NaOEt 2) Q CH₂CH3 3) H3O+

A: The question is based on organic reactions. we need to identify the product formed and explain…

Q: 2. Fill in the boxes in the following problem. (Hints: The difference between the # of carbons in…

A: The missing reactant, reagents and product has find with proper explanation. Also we have provided…

Q: The following ¹H NMR spectrum is shown in two questions. "nmrsim presentation 1 1…

A: Every nuclei will have spin and if an external magnetic field is applied, there will be an energy…

Q: Based on this retrosynthetic analysis, propose a synthesis of the anticoagulant (a substance that…

A: Diphenadione can be produced from the retrosynthetic reaction of diethyl pthalate and the given…

Q: The following three-step reaction was carried out on an unknown reactant to produce a product with…

A: Solution -

Q: 4. How would you use ¹H NMR to distinguish between the following pairs of isomers? Selfosqe AMMO and…

A: Number of signals in 1H NMR = Number of sets of proton in different electronic environment

Q: NaOH + Compound C Compound D MW: C12H140 H. H20 'H NMR of Compound D 3H 3H 2H 1H singlet 5H 7 6. 3 2…

A: Aldol condensation: The given reaction is an example of aldol condensatation. The alpha hydrogen of…

Q: 13C NMR C„H,O2 |(CH2) (CH2) (CH2) السlبuwبسuulسيlسيسيسwuwwlيwlيبuuuluuwيسلسwwwبluuuuuulسلuسلسيسبيا…

Q: Show all the steps and labels for full credit. 8 Propose a structure for the following: C6H13Br. NMR…

Q: Hello can I get help please? I am confused. Thank you!!

A: Step 1: 1H NMR1H NMR (proton nuclear magnetic resonance spectroscopy) is a powerful analytical…

Q: Propose a reagent or reagents for Steps 2–7 and 9.

A: Propose a reagent or reagents for Steps 2–7 and 9.

Q: Carbon NMR Spectrum A has peaks at delta 71, 40, 19, and 12. Spectrum B has peaks at delta 72, 38,…

A: According to the given data we have Spectrum A and spectrum B whose C NMR values are being given…

Q: Provide the correct product for the following series of transformation. Hint: The product has a 1H…

Q: Propose a structure for an amine of formula C,H,N, which liberates a gas when treated with NaNO, and…

A: The NMR spectroscopy is an important tool for the determination of the structure of an organic…

Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

Reaction between this aldehyde and ketone in base gives a compound A with the
proton NMR spectrum: ô 1.10 (9H, s), 1.17 (9H, s), 6.4 (1H, d, J 15), and 7.0 (1H, d, J
15). What is its structure? (Don't forget stereochemistry!). When this compound
reacts with HBr it gives compound B with this NMR spectrum: õu 1.08 (9H, s), 1.13
(9H, s), 2.71 (1H, dd, J 1.9, 17.7), 3.25 (dd, J10.0, 17.7), and 4.38 (1H, dd, J 1.9, 10.0).
Suggest a structure, assign the spectrum, and give a mechanism for the formation
of B.
H
base
C11H₂00
HBr
B
C11H₂1 Bro

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1: Introduce the Reaction:

VIEW

Step 2: Illustrate Formation of A:

VIEW

Step 3: Illustrate Formation of B:

VIEW

Step 4: Assign the Spectrum to A and B:

VIEW

Solution

VIEW

Step by step

Solved in 5 steps with 6 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

3. Compound A (C,H,0) can be reduced to compound B (C,Hg0) with LIA1H. The nmr spectrum of compound B is given below. Write structures for compounds A and B. A (3 HGO) Li Al Hy. + £ दHzo) 200 200 00 TMS
1. Propose the structure of a compound that exhibits the following 'H NMR data: a. CsH10O 1.09 8 (6H, doublet) 2.128 (3H, singlet) 2.588 (1H, septet) b. CH2O 0.91 8 (3H, triplet) 1.198 (6H, singlet) 1.50 8 (2H, quartet) 2.24 ō (1H, singlet)
4
A substituted styrene derivative has the following 'H NMR data: 1H NMR (CDCI3, 400 MHz) 8 8.37 (d, 2H), 8.03(d, 2H), 6.86 (dd, 1H), 6.05 (d, 1H), 5.55 (d, 1H). The structure of styrene itself is C6HsCH=CHz. Which styrenederivative is it? which one is it 2-Fluorostyrene2-Nitrostvrene4-Fluorostyrene 3-Hydroxystyrene4-Nitrostyrene
4. The 1H NMR spectrum shown below corresponds to one of the molecules A-D. Identify the molecule and then provide the complete IUPAC name for the molecule. Don't forget about stereochemistry. он ÕH ÕH B D 11 10 8 6 5 1 'H NMR: 3.35 (1H, m), 1.66 (1H, m), 1.36 (9H, m, overlapping signals), 0.91 (6H, d), 0.90 (3H, t)
Hello can I get help please? I am stuck. Thanks!
Deduce the structure of an unknown compound using the data. C,H,O: 10 NMR: 8 9.8 (1 H, s), 8 1.1 (9 H, s)
7
14. Propose structure for a compound, C9H₁1Br that fits the following ¹H NMR data: 2.15 8 (2H, quintet) 2.75 8 (2H, triplet) 3.38 8 (2H, triplet) 7.22 8 (5H, singlet)
A C5H8 alkyne is reacted with Lindlar's catalyst and hydrogen gas to yield product with the following H NMR resonances. Provide the structure for Product A and the alkyne 0.78 ppm triplet 3H 1.60 ppm doublet 3H 2.05 ppm doublet of quartets 2H 5.40 ppm doublet of quartets 1H 5.34 ppm doublet of triplets 1H
How do you draw the reaction scheme for this?