Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 12.SE, Problem 14AP
Propose structures for compounds that fit the following mass-spectral data:
(a) A hydrocarbon with M+=132
(b) A hydrocarbon with M+=166
(c) A hydrocarbon with M+=84
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Write the contributing resonance structures and resonance hybrid for each of the following:
(a) CH;CH=CH-CH=OH
(f)
CH3
(b) CH2=CH-CH-CH=CH2
(g) CH3-S-CH,
(h) CH3-NO,
(d) CH2=CH-Br
CH,
(e)
Compound X, isolated from lanolin (sheep’s wool fat), has the pungent aroma of dirty sweat socks. A careful analysis showed that compound X contains 62.0% carbon and 10.4% hydrogen. No nitrogen or halogen was found.(a) Compute an empirical formula for compound X.(b) A molecular weight determination showed that compound X has a molecular weight of approximately 117. Find the molecular formula of compound X.(c) Many possible structures have this molecular formula. Draw complete structural formulas for four of them
(a)
(b)
1. CH3MgBr
2. H3O+
H3C OH
I
H3C-C-C-CH3
H3C H
ОН
H
CH3
CH3
H3C CH3
H3C
H₂SO4
C=C
Chapter 12 Solutions
Organic Chemistry
Ch. 12.2 - Prob. 1PCh. 12.2 - Two mass spectra are shown in FIGURE 12-8. One...Ch. 12.3 - What are the masses of the charged fragments...Ch. 12.3 - Prob. 4PCh. 12.5 - Prob. 5PCh. 12.5 - Prob. 6PCh. 12.7 - What functional groups might the following...Ch. 12.7 - How might you use IR spectroscopy to distinguish...Ch. 12.8 - Prob. 9PCh. 12.8 - Where might the following compounds have IR...
Ch. 12.8 - Where might the following compound have IR...Ch. 12.SE - Prob. 12VCCh. 12.SE - Show the structures of the fragments you would...Ch. 12.SE - Propose structures for compounds that fit the...Ch. 12.SE - Write molecular formulas for compounds that show...Ch. 12.SE - Camphor, a saturated monoketone from the Asian...Ch. 12.SE - The nitrogen rule of mass spectrometry says that a...Ch. 12.SE - In light of the nitrogen rule mentioned in Problem...Ch. 12.SE - Nicotine is a diamino compound isolated from dried...Ch. 12.SE - The hormone cortisone contains C, H, and O, and...Ch. 12.SE - Halogenated compounds are particularly easy to...Ch. 12.SE - Prob. 22APCh. 12.SE - Propose structures for compounds that fit the...Ch. 12.SE - 2-Methylpentane (C6H14) has the mass spectrum...Ch. 12.SE - Assume that you are in a laboratory carrying out...Ch. 12.SE - What fragments might you expect in the mass...Ch. 12.SE - How might you use IR spectroscopy to distinguish...Ch. 12.SE - Would you expect two enantiomers such as...Ch. 12.SE - Would you expect two diastereomers such as meso-2,...Ch. 12.SE - Propose structures for compounds that meet the...Ch. 12.SE - How could you use infrared spectroscopy to...Ch. 12.SE - Prob. 32APCh. 12.SE - At what approximate positions might the following...Ch. 12.SE - How would you use infrared spectroscopy to...Ch. 12.SE - At what approximate positions might the following...Ch. 12.SE - Assume that you are carrying out the dehydration...Ch. 12.SE - Assume that you are carrying out the base-induced...Ch. 12.SE - Prob. 38APCh. 12.SE - Carvone is an unsaturated ketone responsible for...Ch. 12.SE - Prob. 40APCh. 12.SE - The mass spectrum (a) and the infrared spectrum...Ch. 12.SE - The mass spectrum (a) and the infrared spectrum...Ch. 12.SE - Propose structures for compounds that meet the...Ch. 12.SE - 4-Methyl-2-pentanone and 3-methylpentanal are...Ch. 12.SE - Grignard reagents undergo a general and very...Ch. 12.SE - Ketones undergo a reduction when treated with...Ch. 12.SE - Nitriles, R–=C≡N, undergo a hydrolysis...Ch. 12.SE - The infrared spectrum of the compound with the...Ch. 12.SE - The infrared spectrum of the compound with the...Ch. 12.SE - Prob. 50AP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Give the systematic name for each of the following; (b) (a) (d) CH3 I CH3-C-CH2-CH3 I CH3 CH3 CH3-CH2-CH-CH=CH2 CH3 I CH3-CH₂-CH-CH-CH3 I CH₂ I CH3 (e) (c) CH3 I CH3-CH₂-CH=C-CH-CH3 I CH3 -CH3 CH₂CH3arrow_forwardDetermine the number of hydrogen atoms in each compound, given the number and type of nonhydrogen atoms it contains and its IHD.(a) Four carbon atoms; IHD = 0(b) Four carbon atoms; IHD =2(c) Three carbon atoms; two oxygen atoms; IHD = 1(d) Five carbon atoms; two chlorine atoms; one nitrogen atom; IHD = 3(e) One carbon atom; one nitrogen atom; IHD = 2(f) Six carbon atoms; two nitrogen atoms; one oxygen atom; three fluorine atoms; IHD = 4arrow_forwardName the following compounds: (a)(b)(c)arrow_forward
- A medicinal chemist at Orgalex Labs, a little known division of a big international pharmaceutical firm, has predicted the major product of the following reacti an early step in the synthesis of Compound R40 (rumored to be a cure for rhinitis, spontaneous combustion, and bad luck): or=0x0 HBr OH As Vice-President of Research, it's your job to decide whether the chemist has made a reasonable prediction. • If your answer is yes, these could be the major products of the reaction, draw the complete mechanism for the reaction below. • If your answer is no, check the box under the drawing area. Ö U OH Br H-Br Add/Remove step Click and drag to start drawing a structure.arrow_forward(i) State reagents G and J. (ii) Draw the structural formula for compounds D, E and H.arrow_forwardthe compound B C23H46,a sex attractant of the common housefly,gave two products Ch3(cH2)12COOH and CH3(CH2)7COOH. Based on this information, suggest the likely structures of Barrow_forward
- Which of the follwoing compounds is responsible for the mass sepctrum and why? (a) octanol, CH3CH2CH2CH2CH2CH2CH2CH2OH (b) heptane, CH3CH2CH2CH2CH2CH2CH3 (c) acetic acid, CH3COOHarrow_forwardThere are two C–C single bonds in penta-1,3-diyne. (a) Which of those bonds would you expect to be stronger? (b) Which of those bonds would you expect to be shorter? (c) The molecule is moderately polar, with a dipole moment of 1.37 D. In which direction would you expect the dipole moment to point? Explain. Penta-1,3-diynearrow_forwardCalculate the number of degrees of unsaturation for each molecular formula, and propose two possible structures: (a) C8H12; (b) C10H10.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY