(a)
To determine: The logical fragmentation reactions to account for the given ion observed in the mass spectra.
Interpretation: The logical fragmentation reactions to account for the given ion observed in the mass spectra are to be given.
Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.
Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number. Fragmentation produces the most stable carbocation and radicals when occurs in
(b)
To determine: The logical fragmentation reactions to account for the given ion observed in the mass spectra.
Interpretation: The logical fragmentation reactions to account for the given ion observed in the mass spectra are to be given.
Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.
Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number. Fragmentation produces the most stable carbocation and radicals when occurs in alkane, but fragmentation at branching is mostly favoured.
(c)
To determine: The logical fragmentation reactions to account for the given ion observed in the mass spectra.
Interpretation: The logical fragmentation reactions to account for the given ion observed in the mass spectra are to be given.
Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.
Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number. Fragmentation produces the most stable carbocation and radicals when occurs in alkane, but fragmentation at branching is mostly favoured.
(d)
To determine: The logical fragmentation reactions to account for the given ion observed in the mass spectra.
Interpretation: The logical fragmentation reactions to account for the given ion observed in the mass spectra are to be given.
Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.
Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number. Fragmentation produces the most stable carbocation and radicals when occurs in alkane, but fragmentation at branching is mostly favoured.
(e)
To determine: The logical fragmentation reactions to account for the given ion observed in the mass spectra.
Interpretation: The logical fragmentation reactions to account for the given ion observed in the mass spectra are to be given.
Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.
Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number. Fragmentation produces the most stable carbocation and radicals when occurs in alkane, but fragmentation at branching is mostly favoured.
(f)
To determine: The logical fragmentation reactions to account for the given ion observed in the mass spectra.
Interpretation: The logical fragmentation reactions to account for the given ion observed in the mass spectra are to be given.
Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.
Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number. Fragmentation produces the most stable carbocation and radicals when occurs in alkane, but fragmentation at branching is mostly favoured.
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Chapter 12 Solutions
Organic Chemistry (9th Edition)
- The infrared spectrum of a compound has a strong absorption at 1669 cm. The mass spectrum of the compound is provided below. What is the structure of the compound? 100 - 80 - 60 40 20 0- 50 75 100 125 m/z OH NH2 Relative Intensityarrow_forwardDraw the mechanism for the following reaction: Et - OH x+a CH3 CH₂ Et Edit the reaction by drawing all steps in the appropriate boxes and connecting them with reaction arrows. Add charges where needed. Electron-flow arrows should start on the electron(s) of an atom or a bond and should end on an atom, bond, or location where a new bond should be created.arrow_forwardOne way to determine the number of acidic hydrogens in a molecule is to treat the compound with NaOD in D2O, isolate the product, and determine its molecular weight by mass spectrometry. For example, if cyclohexanone is treated with NaOD in D2O, the product has MW = 102. Explain how this method works.arrow_forward
- Halogenated compounds are particularly easy to identify by their mass spectra because both chlorine and bromine occur naturally as mixtures of two abundant isotopes. Recall that chlorine occurs as 35Cl (75.8%) and 37Cl (24.2%); and bromine occurs as 79Br (50.7%) and 81Br (49.3%). At what masses do the molecular ions occur for the following formulas? What are the relative percentages of each molecular ion? (a) Bromomethane, CH3Br (b) 1-Chlorohexane, C6H13Clarrow_forwardCompound C is? Compound C-DEPT 135 90 H3C I 70 CH3 CH 4 I 8 (ppm) CI CH₂CH₂CH-Cl CH₂ CH3 CH3-C-CH3 I Cl 1 I 30 10 CH3CH₂CH₂CH₂-Clarrow_forward2. For each of the chemical substitution reactions below identify the major products and whether the reaction is likely an SN1 or SN2. CN SN2 Br NACN ethanol-water NalN 0- Br CN CH,OH / H2O он но SNI Nal (1 equiv.) cl CI acetone SN2 SN' CH;CH,OH 25°C 3. For each of the following compounds provide appropriate reactants and solvent SN2 systems to synthesize them by a substitution reaction. Show which type of substitution: SN1 or Sn2. cannor undero Br NH2 Br NACN NH3 açetone CN ,2 can Br OH HBr SMper NASH Br DMSO -SH Nut SN nappinyarrow_forward
- A. Mel B B. Na, NH3 (1) C. Br2, hv Transformation A: A D L D. NaNH2 E. H₂, Lindlar's cat. F. H₂, Pt G. HBr (1 equiv.) H. 1) xs NaNH2; 2) H,O I. 1) RCO3H; 2) H3O+ Transformation B:arrow_forwardReagents Available g. CO, HCI, CUCI/AICI3 h. CH3CH2CH2COCI, AICI3 i. BrCH2CH2Br, Он j. CH3CH2CI, AICI3 k. RCO3H I. H3O* a. CH2=CHCH,CI, AICI3 b. CH2B12, OH c. CH3CH2COCI, AICI3 d. H2, Pt e. NBS, CCI4 f. K* tBuO Using conditions from the table, show how you would synthesize this compound from catechol (1,2-benzenediol). Select reagents from the table in the order that you wish to use them, i.e. aced; do not include punctuation or spaces If more than one route exists, choose the shorter one; in no case will a synthesis require more than 5 steps.arrow_forwardComplete the following reactions: а. H Mg H,0 H3C. Et,0 ČH3 b. H3C KCN CI H3C с. + CH;0 Na H, C- CH,– Br. d. H3C KMNO 4 он H;C е. он CH3 KMNOarrow_forward
- Reagents a. CeHsCHO b. NaOH, ethanol c. Pyrrolidine, cat. H* j. Brz, H* d. H2C=CHCN e. H3O* f. h. BRCH2CH=CH2 i. Na* OEt, ethanol k. K* t-Buo I. CH2(CO,Et)2 m. heat CH2CH2CN LDA g. ELOC(=0)COEt Select reagents from the table to synthesize this compound from cyclopentanone. Enter the letters of the chosen reagents, in the order that you wish to use them, without spaces or punctuation (i.e. geda).arrow_forward1. Hg(OAc)2/THF/H2O ? d) 2. NaBH,ГОн .CO2C2H5 isi ? e)arrow_forwardIn IR absorption spectra of a compound, strong absorptions at 3300 cm and 2100 to 2260 cm were observed. What functional group might the compound contain? a. Alkyne b. Alkene с. Alcohol d. Carboxylic acidarrow_forward
