Heating the oxetane below to 560°C gives two products A and B (Scheme 2) A + CI Oxetane Scheme 2 The spectroscopic data for A and B is as follows. A - IR 1640cm1, m/z 138 (100%), 140 (33%); dH (ppm) 7.1 (4H,s), 6.5 (1H, dd, J= 17, 11HZ), 5.5 (1H, dd, J= 17, 2Hz), 5.1 (1H, dd, J= 11, 17HZ). B- IR 1700cm1, m/z 111 (45%), 113 (15%), 139 (60%), 140 (100%), 141(20%), 142 (33%); dH (ppm) 9.9 (1H, s) 7.75 (2H, d, J = 9Hz), 7.43 (2H, d, J = 9Hz). a) Suggest the structures for both products A and B. b) Show the mechanism by which they may be formed.

Heating the oxetane below to 560°C gives two products A and B (Scheme 2) A + CI Oxetane Scheme 2 The spectroscopic data for A and B is as follows. A - IR 1640cm1, m/z 138 (100%), 140 (33%); dH (ppm) 7.1 (4H,s), 6.5 (1H, dd, J= 17, 11HZ), 5.5 (1H, dd, J= 17, 2Hz), 5.1 (1H, dd, J= 11, 17HZ). B- IR 1700cm1, m/z 111 (45%), 113 (15%), 139 (60%), 140 (100%), 141(20%), 142 (33%); dH (ppm) 9.9 (1H, s) 7.75 (2H, d, J = 9Hz), 7.43 (2H, d, J = 9Hz). a) Suggest the structures for both products A and B. b) Show the mechanism by which they may be formed.

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: Pease indicate the compound that best fits in the blank of the separation scheme below. OH но, H2N…

Q: A chemist was trying to synthesize compound C over the course of two steps, butafter the first step…

A: Step 1: Step 2:

Q: (c) Propose reagents and conditions for the following 3-step synthesis of secondary amine 10,…

A: We have find out the reagents and conditions for the 3-step synthesis of secondary amine.

Q: C9H9N IR (cm-1): 1H NMR (5): 13C NMR (5): 3050, 2950, 2240, 1630 7.5 (2H, d), 7.1 (2H, d), 2.3 (2H,…

Q: (18) shown below? Which of the following options represents the HOMO for the pentadienyl anion, go…

A: Here we need to determine the Highest Occupied Molecular Orbital (HOMO) of pentadienyl…

Q: A) Phenol Red is a weakly acidic dye which is yellow in the HA form and red in the A form. What…

Q: Compound K: molecular ion at 88; IR peak at 3600-3200 cm-1; 1H NMR data (ppm) at 0.9 (triplet, 3H),…

Q: Treatment of the bicyclic chloride A with lithium in tetrahydrofuran (THF) gave the monocyclic…

A: We have find out the answer.

Q: e. Primary amine 2: A compound C5 H1 00 gave the following spectral da 1H NMR spectrum doublet,…

Q: Deduce the structures of compound A,B,C and D

A: Pyridinium chlorochromate (PCC) is mainly used to oxidation of the primary alcohol into the aldehyde…

Q: here are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following…

A: Isomer A δ (ppm) Splitting pattern No of Hydrogen 0.84 doublet (d) 12 H 1.39 septet 2H…

Q: OH P Q OH HQ HO

Q: Provide a structure for the compound with molecular formula C5H₁00 and with the following…

Q: Liquid hexane (CH3(CH2),CH;) will react with gaseous oxygen (O,) to produce gaseous carbon dioxide…

Q: [Answer All Parts] [50 Marks] Part (a) The following compound 1 shows anticancer activity through…

A: The objective of the question is to propose a workplan for identifying the pharmacophore for…

Q: Propose a structural formula for compound A, C,HO, consistent with its 'H-NMR and IR spectra.…

Q: Provide the missing component that completes the following reactions. (a) (b) (c) (d) 1) BH3, THF 2)…

Q: Compare the conformational profile of butane (A) with that of 1,2-dibromoethane (B) While the methyl…

Q: Complete the following answer using the data provided here: • Molecular formula: CSH1002 • Important…

A: we first need to see the it data which gives the idea about functional group. And NMR data will help…

Q: Provide a structure for the given compound. UV spectrum: Amax = 272 nm (e = 39500); EI mass…

A: The objective of the question is to determine the structure of a compound using the given…

Q: 200 CO C²³- NMR- (Solid Unknown) 180 160 140 120 100 80 60 40 20 0

A: The question is based on the concept of organic spectroscopy. We need to analyse the spectral data…

Question

100%

Expert Solution

This question has been solved!

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

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 2 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Selection Rules for Pericyclic Reactions

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

8. (6) Deduce the identity of the following compound from the IH NMR data given and IR data. C6H8O4: ¿ 3.9 (6H, singlet), 6.1 (2H, singlet) (ppm) IR: 3100 cm', 2950 cm', 1735 cm'
Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?
(b) The 1H-NMR spectrum of compound B, C5 H10 O2, consists of the following signals: 8 1.2 (d, 6H), 2.0 (s, 3H), and 5 (septet, 1H); contains an ester. Draw the structural formula of compound B. • You do not have to consider stereochemistry. • Explicitly draw all H atoms. ୫) C n ? ChemDoodle ® Show Hint
Give the molecular structures of reagent or products for the following chemical reactions: (1) KMNO4, HO, heat PC15 (i) LIAIH(O-t-Bu)3, Et,O, -78°C H;O (A) (B) (C) (а) (ii) H2O OH SOCII, NaCN (i) DIBAL-H, Hexane (E) (F) HCN (b) (ii) H20 (G) (i) DIBAL-H, Hexane HO. (i) LIAIH4 (H) (I) (c) (ii) H2O (ii) H2O
Which of the following statements concerning compounds Y and Z is false? Y Compounds Y and Z are constitutional isomers Compound Y has a lower boiling point than compound Z Compound Y is achiral, while compound Z is chiral Compound Y's parent chain is named as a nonane, while compound Z's parent chain is named as a hexane
The primary amine isoamylamine (3-methylbutylamine) occurs naturally in a number of fruits and is used as a food flavouring: (CH3),CHCH,CH,NH, 3-methylbutylamine Suggest two ways in which it can be synthesised from suitable organic precursors. Note that only one of the two methods you propose may involve the reduction of another nitrogen containing compound. In each case, you should indicate what starting material and other reagents are needed, though details of precise experimental conditions or reaction mechanisms are not required.
Do not give handwriting solution.