Interpretation:
The flowchart of reaction chain and the stereochemical formulas for A, B, C and D are to be proposed and the reactions involved in the transformations are to be outlined.
Concept introduction:
Addition of hydrogen halides is by anti-addition mechanism, which produces structural isomers.
Oxidation of
Two carbonyl groups form in place of one double bond present in the alkene
Potassium tert-butoxide (t-BuOK) is a bulky reagent. It reacts with
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Organic Chemistry
- The reaction of 3,4-dimethyl-3-hexanol (3,4-dimethylhexan-3-ol) with HBr generates compound A as the major product. Treatment of compound A with a strong base gives two isomers of compound B as the major product, along with one isomer of compound C and one isomer of compound D as minor products, all of which have one double-bond equivalent. Identify compounds A, B, C, and D and give their names. By what mechanism does the reaction of 3,4-dimethyl-3-hexanol with HBr occur? By what mechanism does the reaction of A with strong base to form B occur? Propose reaction conditions for an alternative, one-step method for converting 3,4-dimethyl-3-hexanol directly to compound B.arrow_forwardCompound X is optically inactive and has the formula C 16H 16Br 2. On treatment with strong base, X gives hydrocarbon Y, C 16H 14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment Z, is an aldehyde with formula C 7H 6O. The other fragment is glyoxal, (CHO)2. Which of the following answers is correct? Select all that are correct.arrow_forwardCompound X is optically inactive and has the formula C 16H 16Br 2. On treatment with strong base, X gives hydrocarbon Y, C 16H 14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment Z, is an aldehyde with formula C 7H 6O. The other fragment is glyoxal, (CHO)2. Which of the following answers is correct? Select all that are correct.arrow_forward
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- An unknown compound A (molecular formula C7H14O) was treated withNaBH4 in CH3OH to form compound B (molecular formula C7H16O).Compound A has a strong absorption in its IR spectrum at 1716 cm−1.Compound B has a strong absorption in its IR spectrum at 3600−3200cm−1. The 1H NMR spectra of A and B are given. What are the structuresof A and B?arrow_forwardCompounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1. 1.Based on the information provided, determine the structure of compounds B and C. 2.Assign all peaks in 1H NMR spectrum of compounds B and C.arrow_forwardb) Compound A, C;H14 undergo hydration to form B which is optically active. Compound A reacts with cold alkaline potassium manganate (VII) to form C. Ozonolysis of compound A forms methanal and 3,3-dimethylbutanal. Deduce structure A, B, and C.arrow_forward
- (c) Answer each of the questions below that relate to acetophenone: Xo (i) (ii) (iii) Draw the structure of the enol form of acetophenone. Give a stepwise mechanism for the conversion of acetophenone into its enol form. Show how each of the three compounds A, B and C below can be prepared from acetophenone. Explain clearly what reactants/reagents would be required in each case. odocor A B Br Carrow_forwardA chiral amine A having the R configuration undergoes Hofmann elimination to form an alkene B as the major product. B is oxidatively cleaved with ozone, followed by CH3SCH3, to form CH2 = O and CH3CH2CH2CHO. What are the structures of A and B?arrow_forwardAmines suitable for preparing buffers are often synthesized by treating ammonia with epoxides. Consider the following series of reactions, and draw the structure of compound B. NH₂ B You do not have to consider stereochemistry.arrow_forward
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