[{"data":1,"prerenderedAt":-1},["ShallowReactive",2],{"detail-sidebar-cat-0-en-105":3,"doc-seo-348171-105":59,"doc-detail-348171-en":131},{"code":4,"msg":5,"data":6},0,"success",[7,13,18,23,28,33,38,43,48,51,55],{"id":8,"doc_module":4,"doc_module_name":9,"category_name":10,"show_sort_weight":11,"slug":12},1,"Document","Story & Novel",90,"story-novel",{"id":14,"doc_module":4,"doc_module_name":9,"category_name":15,"show_sort_weight":16,"slug":17},2,"Literature",80,"literature",{"id":19,"doc_module":4,"doc_module_name":9,"category_name":20,"show_sort_weight":21,"slug":22},4,"Exam",70,"exam",{"id":24,"doc_module":4,"doc_module_name":9,"category_name":25,"show_sort_weight":26,"slug":27},5,"Comic",60,"comic",{"id":29,"doc_module":4,"doc_module_name":9,"category_name":30,"show_sort_weight":31,"slug":32},6,"Technology",50,"technology",{"id":34,"doc_module":4,"doc_module_name":9,"category_name":35,"show_sort_weight":36,"slug":37},7,"Healthcare",40,"healthcare",{"id":39,"doc_module":4,"doc_module_name":9,"category_name":40,"show_sort_weight":41,"slug":42},8,"Research & Report",30,"research-report",{"id":44,"doc_module":4,"doc_module_name":9,"category_name":45,"show_sort_weight":46,"slug":47},9,"Religion & Spirituality",20,"religion-spirituality",{"id":46,"doc_module":4,"doc_module_name":9,"category_name":49,"show_sort_weight":46,"slug":50},"World Cup","world-cup",{"id":52,"doc_module":4,"doc_module_name":9,"category_name":53,"show_sort_weight":52,"slug":54},10,"Lifestyle","lifestyle",{"id":56,"doc_module":4,"doc_module_name":9,"category_name":57,"show_sort_weight":24,"slug":58},19,"General","general",{"code":4,"msg":60,"data":61},"ok",{"site_id":62,"language":63,"slug":64,"title":65,"keywords":66,"description":67,"schema_data":68,"social_meta":124,"head_meta":126,"extra_data":128,"updated_unix":130},105,"en","chemistry-233-chapter-13-nmr-spectroscopy-problem-set-chapter-13-problem-set","Chemistry 233 - Chapter 13: NMR Spectroscopy Problem Set - Chapter 13 Problem Set","","Chemistry 233 Chapter 13 provides a problem set focused on interpreting NMR spectroscopy data. Questions require identifying distinct hydrogen environments and predicting numbers of 1H NMR signals, comparing downfield shifts, ordering chemical shifts, and determining proton splitting patterns. Additional tasks use 13C NMR and IR data to deduce or propose molecular structures, including diesters, reactions producing spectroscopically characterized products, and estimating rough 1H NMR spectra from structural candidates. Challenge items address reaction outcomes, resonance effects on vinyl proton shifts, isotope labeling, and cubane’s molecular formula and degrees of unsaturation.",{"@graph":69,"@context":123},[70,84,106],{"@type":71,"itemListElement":72},"BreadcrumbList",[73,77,79,82],{"item":74,"name":75,"@type":76,"position":8},"https://docshare.wps.com","Home","ListItem",{"item":78,"name":9,"@type":76,"position":14},"https://docshare.wps.com/document/",{"item":80,"name":20,"@type":76,"position":81},"https://docshare.wps.com/document/exam/",3,{"item":83,"name":65,"@type":76,"position":19},"https://docshare.wps.com/document/chemistry-233-chapter-13-nmr-spectroscopy-problem-set-chapter-13-problem-set/348171/",{"url":83,"name":65,"@type":85,"image":86,"author":91,"headline":65,"publisher":94,"fileFormat":97,"inLanguage":63,"description":67,"dateModified":98,"datePublished":99,"encodingFormat":97,"isAccessibleForFree":100,"interactionStatistic":101},"DigitalDocument",{"url":87,"@type":88,"width":89,"height":90},"https://docshare.wps.com/thumbnails/chemistry-233-chapter-13-nmr-spectroscopy-problem-set-chapter-13-problem-set/348171.png","ImageObject",300,407,{"name":92,"@type":93},"Logic","Person",{"url":74,"name":95,"@type":96},"DocShare","Organization","application/pdf","2026-11-08","2026-09-22",true,{"@type":102,"interactionType":103,"userInteractionCount":105},"InteractionCounter",{"@type":104},"ViewAction",37,{"@type":107,"mainEntity":108},"FAQPage",[109,115,119],{"name":110,"@type":111,"acceptedAnswer":112},"What is the main skill assessed in this NMR spectroscopy problem set?","Question",{"text":113,"@type":114},"The problem set assesses how to interpret 1H and 13C NMR data to predict signal counts, chemical shifts, and splitting, and then use that information—often with IR data—to infer or propose molecular structures.","Answer",{"name":116,"@type":111,"acceptedAnswer":117},"How do you decide which indicated proton appears farther downfield?",{"text":118,"@type":114},"Use the provided tips: for H-C-Z, the proton moves further downfield as Z becomes more electronegative; for Csp3-H, the proton moves further downfield as the carbon substitution increases (3° > 2° > 1°).",{"name":120,"@type":111,"acceptedAnswer":121},"What additional spectroscopic information is used besides NMR to determine structures?",{"text":122,"@type":114},"The problems frequently include IR spectroscopy data such as C=O stretch positions (e.g., around 1690–1740 cm-1) to help identify functional groups, which complements the NMR signal interpretation for structure determination.","https://schema.org",{"og:url":83,"og:type":125,"og:title":65,"og:site_name":95,"og:description":67},"article",{"robots":127,"canonical":83},"index,follow",{"doc_id":129,"site_id":62},348171,1790270343,{"code":4,"msg":5,"data":132},{"doc_id":129,"user_id":133,"nickname":92,"user_avatar":134,"doc_module":4,"category_id":19,"category_name":20,"doc_title":65,"doc_description":67,"doc_content":135,"file_id":136,"file_url":137,"file_type":138,"file_size":139,"view_count":105,"is_deleted":4,"is_public":8,"is_downloadable":8,"audit_status":8,"page_count":39,"language":140,"language_code":63,"site_id":62,"html_lang":63,"table_of_contents":141,"faqs":142,"seo_title":143,"seo_description":67,"update_tm":144,"read_time":46,"preview_page_count":4},1099513958762,"https://ap-avatar.wpscdn.com/avatar/1000023916a998db790?x-image-process=image/resize,m_fixed,w_180,h_180&k=1784791008015729253","Chemistry 233  \nChapter 13: NMR Spectroscopy Problem Set  \n1) For each compound below, identify each chemically distinct type of hydrogen. Specify the number of 1 H NMR signals you would expect to see.  \n2) Which of the indicated protons in each pair shows up farther downfield?  \nTips: For H-C-Z, H moves further downfield as Z becomes more electronegative For Csp3-H, H moves further downfield as C becomes more substituted (3°>2°>1°)  \nChapter 13 Problem Set 1/8  \n3) Consider the indicated protons in each of the three compounds below. Arrange in order of increasing chemical shift of the indicated proton. See tips in Q2.  \n4) For each of the compounds below, determine the expected splitting for all protons.  \n5) How many 13C signals would you expect each compound below to exhibit? (i.e. How many  \n6) A symmetric diester has the formula C6H10O4 and the following 1 H NMR spectral data: 1.4 7 (d, 3H), 2.07 (s, 6H), 6.84 (q, 1H) . Propose a structure for this compound.  \nChapter 13 Problem Set 2/8  \n7) The reaction shown below was carried out in a laboratory to give a compound with the indicated spectral data. Determine the structure of this compound.  \nO  \nH  \nF  \nOH  \n+ N  \nC11 H 15 NO 2  \nIR stretch at 1730 cm-1  \nEight signals in the 13 C NMR  \n1 H NMR Data: 2.32 (s, 6H), 3.05 (t, 2H), 4.20 (t, 2H), 6.97 (d, 2H), 7.82 (d, 2H), 9.97 (s, 1H)  \n8) For each of the following, use the data provided to deduce an appropriate structure.  \nA. C6H12  \nPPM  \nChapter 13 Problem Set 3/8  \nB. C5H9ClO2 Use the 13 C NMR to determine the number of distinct C atoms. IR spectroscopy shows a strong C=O stretch.  \n1H NMR  \n2H  \n2H  \n3H  \n2H  \n5 4 3 2 1 0  \nPPM  \n\n|  | 13C NMR |  |  |  |  |  |  |\n| --- | --- | --- | --- | --- | --- | --- | --- |\n|  | | | | |  |  |  |\n|  |  |  |  |  |  |  |  |\n\n180 160 140 120 100 80 60 40 20 0  \nPPM  \nC. C6H10    \n\n| 1H NMR\u003Cbr>| | 9H\u003Cbr>\u003Cbr>| |\n| --- | --- | --- | --- |\n| 3 2 1 0 |  |  |  |\n\nPPM  \nChapter 13 Problem Set 4/8  \nD. C4H6O2     \nIR shows a strong stretch at 1740 cm-1  \n1H NMR 2H  \n2H  \n2H  \n4 3 2 1 0  \n5  \nPPM  \nE. C4H8O2 ~~ ~~    \nPPM  \nF. C6H12     \n5  \nPPM  \nChapter 13 Problem Set 5/8  \nG. Compound contains 10C and IR shows a strong stretch around 1690 cm-1  \n5 4 PPM  \nH. C4H9OCl    \n3  \n2 2  \n2  \n4 3 2 1 0  \nPPM  \nChapter 13 Problem Set 6/8  \n9) For each of the compounds below, draw a rough estimation of its expected 1 H NMR spectrum.  \nCl  \nCl  \n Cl  \n I Br    \nChallenge Problems:  \n10)Use the spectral data provided to predict the product of the reaction shown below.  \nOH  \nOH  \nH 3O+  \nH 2O  \n C7H 12O  \nIR: 1729 cm-1  \n1 H NMR: 9.72 (d, 1H), 2.30 (sex, 1H),1 .4-18 (m, 10H)  \nsignals for 10 H overlapping in this region. Some are and some are not equivalent.  \n11) The vinyl proton chemical shift in the two compounds shown below is substantially different.  \nChapter 13 Problem Set  \nExplain why the shift in these two compounds is so different. Hint: think about resonance.  \nO  \nO  \nH  \nH  \nCH3  \n4.0 ppm  \n6.5 ppm  \n7/8  \n12)Propose a structure for a compound with the formula C5H9ClO.  \n1 H NMR Data:  δ 6 . 07 (1H, multiplet) alkene H  \n δ 5.43 (1H, d) alkene H  \nδ 5 . 31 (1H, d) alkene H  δ 4 . 04 (2H, d)  \n δ 3 . 83 (2H, t)    \n δ 3.65 (2H, t)  \n13)A student ran the reaction shown below. What would you expect the structure of the product to be? Given the 1 H NMR of the starting materials, how would you expect it to change following thereaction? Note: D is a heavy isotope of H. It reacts almost identically to H (ie. DCl reacts like HCl).  \nO  \nOH  \n1. NaH  \n2. DCl, D 2O  \nO  \nOH  \n12 10 8 4 2 0  \n6  \nPPM  \n14) The structure of cubane is shown below. What is the molecular formula for cubane? Using the unsaturation calculation, determine the degrees of unsaturation. Now, using visual inspection,  \ndetermine the degrees of unsaturation. You should find that there is a discrepancy. Which number is correct? Can you use an alternate method to confirm your unsaturation count?  \nChapter 13 Problem Set 8/8","cbCaicqcUSOz8knz","https://ap.wps.com/l/cbCaicqcUSOz8knz","pdf",4769932,"English","# Chapter 13: NMR Spectroscopy Problem Set\n## Problem Set Questions\n## Challenge Problems","[{\"question\":\"What is the main skill assessed in this NMR spectroscopy problem set?\",\"answer\":\"The problem set assesses how to interpret 1H and 13C NMR data to predict signal counts, chemical shifts, and splitting, and then use that information—often with IR data—to infer or propose molecular structures.\"},{\"question\":\"How do you decide which indicated proton appears farther downfield?\",\"answer\":\"Use the provided tips: for H-C-Z, the proton moves further downfield as Z becomes more electronegative; for Csp3-H, the proton moves further downfield as the carbon substitution increases (3° \\u003e 2° \\u003e 1°).\"},{\"question\":\"What additional spectroscopic information is used besides NMR to determine structures?\",\"answer\":\"The problems frequently include IR spectroscopy data such as C=O stretch positions (e.g., around 1690–1740 cm-1) to help identify functional groups, which complements the NMR signal interpretation for structure determination.\"}]","Chemistry 233 - Chapter 13: NMR Spectroscopy Problem Set - Chapter 13 Problem Set | PDF",1790071482]