1 Structure And Bonding 2 Acids And Bases 3 Introduction To Organic Molecules And Functional Groups 4 Alkanes 5 Stereochemistry 6 Understanding Organic Reactions 7 Alkyl Halides And Nucleophilic Substitution 8 Alkyl Halides And Elimination Reactions 9 Alcohols, Ethers, And Related Compounds 10 Alkenes 11 Alkynes 12 Oxidation And Reduction 13 Mass Spectrometry And Infrared Spectroscopy 14 Nuclear Magnetic Resonance Spectroscopy 15 Radical Reactions 16 Conjugation, Resonance, And Dienes 17 Benzene And Aromatic Compounds 18 Reactions Of Aromatic Compounds 19 Carboxylic Acids And The Acidity Of The O-h Bond 20 Introduction To Carbonyl Chemistry; Organometallic Reagents; Oxidation And Reduction 21 Aldehydes And Ketones-nucleophilic Addition 22 Carboxylic Acids And Their Derivatives-nucleophilic Acyl Substitution 23 Substitution Reactions Of Carbonyl Compounds At The α Carbon 24 Carbonyl Condensation Reactions 25 Amines 26 Carbon–carbon Bond-forming Reactions In Organic Synthesis 27 Pericyclic Reactions 28 Carbohydrates 29 Amino Acids And Proteins 30 Synthetic Polymers 31 Lipids expand_more
Chapter Questions expand_more
Problem 13.1P: What is the mass of the molecular ion formed from compounds having each molecular formula: a C3H6O;b... Problem 13.2P Problem 13.3P: Use the following information to propose a molecular formula for nootkatone, a compound partly... Problem 13.4P Problem 13.5P: What molecular ions would you expect for the compound depicted in the ball-and-stick model? Problem 13.6P: The mass spectrum of 2,3-dimethylpentane also shows peaks at and 43. Propose
possible structures... Problem 13.7P: The base peak in the mass spectrum of 2, 2, 4-trimethylpentane [(CH3)3CCH2CH(CH3)2] occurs at m/z=57... Problem 13.8P: (a) What mass spectral fragments are formed by cleavage of butan-2-ol,
? (b) What fragments are... Problem 13.9P: What cations are formed in the mass spectrometer by cleavage of each of the following compounds? a.... Problem 13.10P: The low-resolution mass spectrum of an unknown analgesic X had a molecular ion of 151. Possible... Problem 13.11P: Benzene, toluene, and p-xylene BTX are often added to gasoline to boost octane ratings. What would... Problem 13.12P Problem 13.13P Problem 13.14P Problem 13.15P Problem 13.16P: How do the IR spectra of the isomers cyclopentane and pent-1-ene differ? Problem 13.17P: Problem 13.17 How do the three isomers of molecular formula ( and ) differ in their IR spectra?
Problem 13.18P: Problem 13.18 What functional groups are responsible for the absorptions above 1500 cm–1 in the IR... Problem 13.19P: Problem-13.19 What are the major IR absorptions in the functional group region for each... Problem 13.20P: Problem-13.20 What are the major IR absorptions in the functional group region for oleic acid, a... Problem 13.21P: Problem-13.21 Which of the following possible structures for X can be excluded on the basis of its... Problem 13.22P: Problem-13.22 Propose structures consistent with each set of data: (a) a hydrocarbon with a... Problem 13.23P: 13.23 What major IR absorptions are present above for each compound?
a. b.
Problem 13.24P: Problem-13.24 The mass spectrum of the following compound shows fragments at = 127, 113, and 85.... Problem 13.25P Problem 13.26P: Which compound gives a molecular ion at m/z= 122, C6H5CH2CH2CH3,C6H5COCH2CH3 or C6H5OCH2CH3. Problem 13.27P: Propose two molecular formulas for each molecular ion: a 102; b 98; c 119; d 74 Problem 13.28P: Propose four possible structures for a hydrocarbon with a molecular ion at m/z=112. Problem 13.29P: Problem-13.29 What is the molecular formula for -himachalene, a hydrocarbon obtained from cedar... Problem 13.30P: Problem-13.30 Propose a molecular formula for rose oxide, a rose-scented compound isolated from... Problem 13.31P: 13.31 Match each structure to its mass spectrum
Problem 13.32P: 13.32 Propose two possible structures for a hydrocarbon having an exact mass of that forms... Problem 13.33P: 13.33 What cations are formed in the mass spectrometer by cleavage of each of the following... Problem 13.34P: 13.34 and have the same molecular ion in the mass spectrum, but
only one of these isomers gives... Problem 13.35P: 13.35 For each compound, assign likely structures to the fragments at each value, and explain... Problem 13.36P Problem 13.37P: 13.37 Propose a structure consistent with each set of data.
a compound that contains a benzene... Problem 13.38P: 13.38 A low-resolution mass spectrum of the neurotransmitter dopamine gave a molecular ion at .... Problem 13.39P: 13.39 Primary alcohols often show a peak in their mass spectra at . Suggest a structure for this... Problem 13.40P: 13.40 Like alcohols, ethers undergo α cleavage by breaking a carbon–carbon bond between an alkyl... Problem 13.41P: 13.41 Which of the highlighted bonds absorbs at higher in an IR spectrum.
a. b. c.
Problem 13.42P: 13.42 What major IR absorptions are present above for each compound?
a. b. c. d.
Problem 13.43P: 13.43 How would each of the following pairs of compounds differ in their IR spectra?
a. c.
b.... Problem 13.44P: 13.44 Morphine, heroin, and oxycodone are three addicting analgesic narcotics. How could IR... Problem 13.45P: 13.45 Reduction of cyclohex-2-enone can yield cyclohexanone, cyclohex-2-enol, or... Problem 13.46P Problem 13.47P: 13.47 Match each compound to its IR spectrum
Problem 13.48P: 13.48 Propose possible structures consistent with each set of data. Assume each compound has an ... Problem 13.49P: A chiral hydrocarbon X exhibits a molecular ion at in its mass spectrum. The IR spectrum of X
... Problem 13.50P: 13.50 A chiral compound has a strong absorption at in its IR spectrum and gives the following mass... Problem 13.51P: 13.51 Treatment of benzoic acid with followed by -iodo--methylbutane forms . has a molecular ion... Problem 13.52P: 13.52 Treatment of benzaldehyde with in aqueous forms a compound that has a molecular ion at in... Problem 13.53P Problem 13.54P: 13.54 Reaction of 2-methylpropanoic acid with followed by 2-methylpropan-1-ol forms . has a... Problem 13.55P: 13.55 Reaction of pentanoyl chloride with lithium dimethyl cuprate forms a compound J that has a... Problem 13.56P Problem 13.57P: 13.57 Treatment of anisole with and forms P, which has peaks in its mass spectrum at , , ,... Problem 13.58P: 13.58 Reaction of with forms compound , which
gives the IR and mass spectra shown below.... Problem 13.59P: Problem-13.59 The carbonyl absorption of an amide typically occurs in the range, while the carbonyl... Problem 13.60P Problem 13.61P: Problem-13.61 Explain why a ketone carbonyl typically absorbs at a lower wave number than an... Problem 13.62P: 13.62 Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of... format_list_bulleted
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning