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1 HWeb27 ( ; ) Which of the following cannot be determined about a compound by mass spectrometry? [a]. boiling point [b]. molecular formula [c]. presence of heavy isotopes (e.g., 2 H, 13 C) [d]. molecular weight Which of the following is used to ionize molecules in mass spectrometry? [a]. by an ionizing magnetic field [b]. by a beam of gamma radiation [c]. by a beam of high energy electrons [d]. by placing the molecules in an electric field Which of the following is not true? [a]. the most intense peak in the mass spectrum of a compound corresponds to its molecular ion [b]. the molecular ion is a radical cation formed upon removal of an electron [c]. the heaviest ion detected by mass spectrometry is the molecular ion [d]. fragmentation is the process whereby molecular ions break up into smaller species

2 HWeb 28 (2.16) What type of compound an IR peak at ~3300 cm -1, but not at ~1720 or 1100 cm -1? [a]. alcohol [b]. carboxylic acid [c]. ketone [d]. ester Which of the following types of compound has a strong IR band in the region of 1700 cm -1? lkane [b]. Alkene [c]. Alcohol [d]. Ketone The combustion analysis of a compound indicates that it has a carbon to hydrogen ratio of one-totwo and that another element is present. The mass spectrum shows a molecular ion at m/z=58. The IR spectrum shows a peaks at approximately 1650 and 1100 cm -1, but no peaks at approximately 1720 or 3300 cm -1. What structure is consistent with this data? H H A B C D

3 HWeb29 ( ) Which of the following is not true regarding nuclear magnetic resonance? [a]. Nuclei act as magnets and align with a magnetic field [b]. Nuclei absorb energy when they flip from being aligned with a magnetic field to being misaligned. [c]. The radioactive decay of nuclei is observed [d]. The technique aids in the determination of organic structures Useful information obtained from a 1 H NMR spectrum include: [a]. chemical shift [b]. integration [c]. splitting [d]. all of the above Which of the following regions of the electromagnetic spectrum corresponds to the energy difference between the spin states of a nucleus in a magnetic field? [a]. gamma rays [b]. X-rays [c]. radio waves [d]. IR

4 HWeb30 ( ) How many signals are there in the 1 H NMR spectrum of 2-methyl-2-pentanol? [a]. Three [b]. Four [c]. Five [d]. Six How many signals are there in the 1 H NMR spectrum of p-xylene (1,4-dimethylbenzene)? [a]. Two [b]. Three [c]. Four [d]. Five How many signals are there in the 1 H NMR spectrum of 1,3,5-trimethylbenzene? [a]. ne [b]. Two [c]. Three [d]. Four

5 HWeb31 (9.8) What type of peaks are there in the 1 H NMR spectrum o-xylene (1,2-dimethylbenzene)? [a]. two singlets [b]. three singlets [c]. a singlet and two doublets [d]. two singlet and a doublets 31.2 What type of peaks would be obtained in a 1 H NMR spectrum of isopropyl formate HC(=)CH(CH 3 ) 3? [a]. three singlets [b]. one quartet, one triplet, one singlet [c]. a singlet, a doublet and a septet [d]. two triplets, one doublet 31.3 What type of peaks would be obtained in a 1 H NMR spectrum of ethyl acetate, CH 3 C 2 CH 2 CH 3? [a]. three singlets [b]. one quartet, one triplet, one singlet [c]. two triplets, one doublet [d]. unable to answer; more information is needed.

6 HWeb32 ( review) What is the structure of the compound, C 4 H 7 2, which has the following NMR spectra? 1 H NMR: 2.89 ppm (triplet, 2H), 3.54 ppm (triplet, 2H), 3.69 ppm (singlet, 3H) 13 C NMR: 25.8 ppm, 37.5 ppm, 52.0 ppm, 171 ppm How many signals appear in the 13 C NMR (broadband proton-decoupled) spectrum of 3- bromobenzoic acid? CH [a]. Four [b]. Five [c]. Six [d]. Seven 32.3 A compound had the following analysis: C=39.75%; H=7.34%; =52.90%. Its 13 C NMR spectrum shows five peaks. What is the correct structure of this compound? A B C D

7 HWeb33 (Spectral Problems) Which of the following compounds (C 6 H 14 N 2 ) gives a 1 H NMR spectrum consisting of three signals and a 13 C NMR spectrum consisting of two peaks? HN CH 3 N H 3 C N N CH 3 H 2 N NH 2 N H 3 C N A B C H D The 1 H NMR spectrum of a compound has signals at approximately 1.2 (t, 3H), 2.5 (q, 2H), 4.0 (s, 3H), and 7-8 (4 H) ppm. Its IR spectrum had prominent peaks at 3050, 2950, and 1700 cm -1. What is the structure of this compound? H 3 C H 3 C CH 2 CH 3 CH 3 A B H 3 CCH 2 CH 3 H 3 C C D CH 2 CH The 1 H NMR spectrum of a compound has signals at approximately 1.2 (t, 3H), 2.5 (q, 2H), 4.0 (s, 3H), and 7-8 (4 H) ppm. Its IR spectrum had prominent peaks at 3050, 2950, and 1700 cm -1. What is the structure of this compound? CH 2 CH 3 CH 3 CH 2 CH 3 CH 3 A B C D 1. A 2. B 3. C 4. D CH 3 CH 3 CH 3 CH 2 CH 3

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