OH NH2 Неpt + CH3SO,CI + CH3(CH2)NHET H3C (a) (b) (c) (d) (c) SOCI2 (a) + (b) H3PO4 OH Et Неpt (d) (i) (h) H3C Work out the details of the above retrosynthesis on a separate sheet of paper, and then draw the structure of (h). • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Include counterions for diazonium salts. opy aste Previous Next

OH NH2 Неpt + CH3SO,CI + CH3(CH2)NHET H3C (a) (b) (c) (d) (c) SOCI2 (a) + (b) H3PO4 OH Et Неpt (d) (i) (h) H3C Work out the details of the above retrosynthesis on a separate sheet of paper, and then draw the structure of (h). • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Include counterions for diazonium salts. opy aste Previous Next

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...

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Reaction of Zn/Hg; HCI ( Clemmensen conditions) with CH3CH2C(O)C6H5 forms ____ as the product. (a) CH3CHCHC6H5 (b) CH3CH2COOH and C6H5COOH (c) CH3CH2CH2OH and C6H5OH (d) CH3CH2CH(OH)C6H5 (e) CH3CH2CH2C6H5
(b) Answer all parts (1) – (). The carbohydrate J forms a six-membered cyclic hemiacetal K that predominates at equilibrium in aqueous solution. но он он = K cyclic hemiacetal ) Assign Ror S configurations to the stereogenic centres in J. (#) Draw the structure for the cyclic hemiacetal K. (i) Using curly arrows show the reaction mechanism for the formation of K.
A key step in the hydrolysis of acetamide in aqueous acid proceeds by nucleophilic addition of * OH (a) H3O* to CH3Ĉ NH2 (b) H2O to CH3ČNH2 + OH +OH (c) H3O* to CH,ČNH2 (d) HO¯ to CH3CNH2
Draw the organic products formed in each of the following reactions. (i). (ii) (iii) (iv) +:C=C-H + H₂O CH₂C=CCH₂CH3 HgSO4, H₂SO4 Na, NH3 2 equiv Br₂ (1) Sia₂BH.THF (2) H₂O₂ NaOH
Answer ALL parts of this question. (a) If ethyne is treated according to the following scheme, the final product is trans-pent-2-ene, as shown: H- (c) C-H (i) NaNH, / NH, (ii) CH₂Br (iii) NaNH, / NH (iv) CH₂CH₂Br (v) Na/NH3 H₂C H H CH₂CH3 Show the structures of the intermediates formed after each of the first four steps and identify the mechanism involved in steps (ii) and (iv). (b) If cis-pent-2-ene was wanted as the final product, how would step (v) in the sequence above must be modified? | The alkene shown in part (a) of this question could also be made by treating 2-bromopentane with base. It would be the major product out of three possible alkenes that could form. Give the structures of the two other alkenes that would form and comment on why trans-pent-2-ene is the major one that forms here.
(d) With reference to the following reaction scheme: H 22 1. Li, NH3, -78 °C BuOH (1 equiv.) 2. NH4CI H "I 23 (i) Explain why only one of the two C-C double bonds in enone 22 is reduced under these reaction conditions. (ii) Draw a curved arrow mechanism for the transformation of 22 into 23.
B) Rank the following species in order of increasing nucleophilicity. (A) CH3CH2S-, (B) CH3CH2O-, (C) (CH3)3CO-, (D) (CH3)3COH.
7B. (2 reactions (should clearly indicate the stereochemistry). Draw the structure of the product, substrate or condition in the following (a) ОН (b) Ме 1) OsO4 2) NaHSO3 (c) 1) (sia)2BH 2) NaOH/H2O2 H20
OH + (b) (c) NH3, NABH,CN (c) (d) C2, H20 NaOH, H20 (d) (а), Н* (b) Work out the details of the above retrosynthesis on a separate sheet of paper, and then draw the structure of (d).
The saccharide shown here is present in some plant-derived foods. (a) Indicate the anomeric carbon atom(s) in this structure by drawing a circle around the atom(s) or by drawing an arrow pointing to the atom(s). (b) Would this saccharide give a positive result with Benedict’s reagent? Why or why not? (c) Would this saccharide give a positive result with Barfoed’s reagent? Why or why not? (d) Would this saccharide give a positive result with Seliwanoff’s reagent? Why or why not? (e) In a separate set of experiments, the saccharide solution was treated with a reagent that breaks glycosidic bonds. After this treatment, would any of the three assays give different results? Be sure to indicate which assay results would be different and give a reason.
The formula of the precursor is given for each of the following reactions. Draw its structure, paying attention to stereochemistry, if appropriate. (a) (b) CI OH NaCI (CH3)3CONA C6H1„BrO C12H1,CI Acetone DMSO
Dichloromethane (CH,Cl,) can be treated with butyllithium, CH3CH,CH,CH,-Li (Bu-Li), to make a carbene in situ, analogous to the way a carbene is generated from trichloromethane (CHCI3) using HO¯. (a) Show the mechanism for the generation of a carbene from CH2CI2. (b) Why is butyllithium used instead of HO-? (c) The reaction shown here leads to a mixture of four products. Draw all four products. CH,Cl, ? Bu-Li Draw the mechanism for this reaction