CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY
8th Edition
ISBN: 2818440043505
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Textbook Question
Chapter 15, Problem 54P
- a. Which compound would you expect to have a greater dipole moment, methyl acetate or butanone?
- b. Which would you expect to have a higher boiling point?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
An ether has a lower boiling point than an aldehyde of the same mass (or number of C atoms). Why is this?
a. the ether, containing a carbonyl group, interacts more strongly (ether molecule to ether molecule) than does an aldehyde (molecule to molecule),
b. The ether, with its single O atom, can H bond to only 2 water molecules.
c. The ether, with its single O atom and no attached H atom, does not form H bonds and does not have a dipole for dipole/dipole interaction.
d. All of the above.
Rank the compounds in each group in order of increasing boiling point.
a. CH3(CH2)4I, CH3(CH2)sI, CH3(CH)gI
b. CH;CH,CH,NH2, (CH3);N, CH3CH2CH,CH3
c. (CHa),COC(CH3)3, CHa(CH2)30(CH)¿CH3, CH3(CH2);OH
COH
d.
HO.
Br
е.
OH
f.
2. a) Draw the structures of Perylene dianhydride, Naphthalene and Salicylic acid
b) Arrange the compounds in order of increasing polarity considering the structures
and Rf values
Chapter 15 Solutions
CHEM 262 ORG CHEM EBOOK DIGITAL DELIVERY
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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
- 6. Show how the following alcohols below can be distinguished. a) butanol and 2- butanol b) 2-propanol and 3- hexanolarrow_forward1. What letter has an aldehyde with molecular formula C₄H₈O. 2. What letter has an ester with molecular formula C₄H₈O₂ 3. What letter has a ketone with molecular formula C₄H₈O₂ 4. What letter has a carboxylic acid with molecular formula C₄H₈O₂arrow_forwardWhich structure is different from the following? a. b. C. d. CH3 н Н CH3 H CH3 CH3 H3C- н CH3 CH3 н H CH3 н Н н CH3 н H Н -CH3 CH3 CH3arrow_forward
- 2. The molecules shown below are four terpineol isomers. They are isolated from plants and have distinct aromas. For example, a -terpineol is a common perfume ingredient and smells similar to lilacs. Hol H-O- a-terpineol B-terpineol Y-terpineol 4-terpineol A) Draw a structural isomer of terpineol that meet the following criteria. You should draw one unique structure for each set. You must draw each molecule twice, once as a skeletal structure and once as a complete Lewis structure showing all atoms, bonds, and lone pairs of electrons. i. Does not have a ring. ii. Has an E alkene. iii. Has a secondary alcohol. iv. Does not contain an alcohol. B) Draw a complete Lewis structure of a-terpineol showing all bonds, atoms and lone pairs of electrons.arrow_forward1. Draw the structure for each compound. a.(3R)-3-methylhexane b. (3R,5S,6R)-5-ethyl-3,6-dimethylnonanearrow_forwardWhich is/are correct? a.The dipole moment of propanal is greater than that of 1-butene. b.Carbonyl compounds are more soluble in water than the corresponding alkanes but less than the corresponding alcohols. c.All the choices. d.The boiling points of 2-propanol, propanone, and 2-methylpropene are 82C, 57C, and -7C, respectively.arrow_forward
- Compare the following two alcohols. Which one is more soluble in water? Why? НО OH Compound 1 OH Compound 2 OH A) Compound 1 is more soluble because it has greater ability to hydrogen bond with water. B) Compound 2 is more soluble because it has greater ability to hydrogen bond with water. C) Neither of these compounds are water soluble. D) Compound 1 is more soluble because it will have more dipole-dipole interactions with water. E) Compound 2 is more soluble because it will have more dipole-dipole interactions with water.arrow_forward3. Explain in 2 sentences why acetic acid is more acidic than butanoic acid.arrow_forwardCH3–C–CH2-CH3 For the compound: a. Circle the carbonyl group in the compound above. b. What is the geometry of the carbon atom of the carbonyl group? What is the hybridization of the carbonyl carbon (sp, sp² or sp³)?. d. Is the compound soluble or insoluble in water? e. Is the compound more or less soluble (in water) than an alcohol? f. Does this compound have a higher or lower bp than an alkane? С.arrow_forward
- 3. Some students also confuse the structure of cyclohexanol with that of a phenol. Both structures have a six-carbon ring with a hydroxyl group attached. Use your learnings from the CHM 124 lecture course to explain how the six-carbon rings of cyclohexanol and phenol are different from one another.arrow_forward10.2 Provide names for the compounds. NO2 GH3 CH,CH2CH3 Br C. b. a.arrow_forward1. Draw two resonance structures for 1,3-cyclopentadiene and naphthalene, respectively. Use appropriate resonance arrows. 1,3-cyclopentadiene Naphthalenearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY