Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 12.SE, Problem 37AP
Assume that you are carrying out the base-induced dehydrobromination of 3-bromo-3-methylpentane (Section 11-7) to yield an
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
The oxidation of 3-pentanol to 3-pentanone was performed in the lab and an IR was taken of the finished product.
(a) what are the key functional groups in the starting material, 3-pentaol?
(b) what are the key functional groups in the product, 3-pentanone?
(c) based on the IR spectrum below, was the experiment successful, and, if so, how pure was the product? Explain your reasoning.
The IR spectrum of a sample contains absorptions at 1750 cm-1. To what class of
organic compound does this sample most likely belong?
Alkene
Ketone
Alkane
Alcohol
Reduction of cyclohex-2-enone can yield cyclohexanone, cyclohex-2-enol, or cyclohexanol, depending on the reagent and reaction conditions. How could you use IR spectroscopy to distinguish the three possible products?
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
- Assume that you are in a laboratory carrying out the catalytic hydrogenation of cyclohexene to cyclohexane. How could you use a mass spectrometer to determine when the reaction is finished?arrow_forwardNitesharrow_forward14. predict the product of the raction below. Which of the following change(s) in the IR spectrum is consistent with conversion of the reactant to productarrow_forward
- Below are three MS spectra, Spectra 1, 2, and 3. Each of this mass spectrum corresponds to either Compound A (contains one Cl in the molecular formula), Compound B (one I in the molecular formula), and Compound C (one Br in the molecular formula). Identify which spectra corresponds to which compound. Provide explanations for your choices.arrow_forwardWhich of the following molecules do you expect would be useful in quenching benzophenone photoreduction? Explain.Oxygen (S1 = 22 kcal/mol)9,10-Diphenylanthracene (T1 = 42 kcal/mol)trans-1,3-Pentadiene (T1 = 59 kcal/mol)Naphthalene (T1 = 61 kcal/mol)Biphenyl (T1 = 66 kcal/mol)Toluene (T1 = 83 kcal/mol)Benzene (T1 = 84 kcal/mol)arrow_forwardPLEASE EXPLAIN AND Assign each spectrum to one compound following two mass spectra represent 1-bromo-4-ethylbenzene and (1-bromoethyl)benzene, respectively.arrow_forward
- The mass spectrum of an alkene, C8H16, exhibits a peak at m/z = 41. Draw two isomers that are consistent with these data.arrow_forward2) For each of the following pairs of compounds, name one absorption band that can be used to distinguish between them. State what the bond is (bond order, between which 2 atoms), and approximately where it appears in the IR spectrum (in cm ¹). b) HO 1-hexanol OH phenol H₂N 1-butanamine ethyl acetate cyclohexane OH hexanoic acid LOH cyclohexanol NH₂ butanamide diethyl ether cyclohexenearrow_forwardWhat is the reactant and the desired product? If you were looking at both of the IR spectrum, where would you confirm that the desired reaction had occured.arrow_forward
- 9) What would be the difference between the 4 alcohols in IR? They all show O-H, C-H sp3, and C-H aromatic bonds. The only way to tell which one is used would be by comparing the fingerprint regions to published IR spectra of each alcohol. Alcohol 2 has an aldehyde C-H group that could be seen between 2700-2800 and 2800-2900 cm-1 Only alcohol 3 will show O-H bond around 3300 cm-1 Only alcohol 1 will show C=C aromatic bonds around 1600 cm-1 10) Assuming 5.0 mL of alcohol 2 was used and 2.2 g of the product was isolated, what is the percent yield for this reaction? The product has a molar mass of 198.00 g/mol. 11) How could the percent yield be increased for this reaction? Add NaOH to neutralize the product as it forms Add a catalyst such as H2SO4 to help speed up the reaction Add a catalyst such as HCl to help speed up the reaction Cool the reaction on ice to increase the rate of reaction 12) Is there another way that the product of this reaction…arrow_forwardWhat type of compound is most consistent with the IR spectrum shown below? 3000 1500 1000 4000 O None of the choices are correct. O carboxylic acid can bị nitrile (i.e., RCN) O ketone O alkene aldehyde esterarrow_forwardNeed in 10minsarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY