
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
expand_more
expand_more
format_list_bulleted
Question
Chapter 19, Problem 35DSP
Interpretation Introduction
Interpretation:
The stereochemistry of the product formed is to be deduced on the basis of the facts given in the reaction.
Concept introduction:
Cyclic esters are called lactones and are often prepared by the intramolecular cyclization of hydroxy substituted
Electrophilic addition to the double bond of unsaturated carboxylic acids gives a lactone.
During iodolactonization,
Anti addition takes place in this cyclization.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
A solution consisting of 0.200 mol methylbenzene, C,H,CH,, in 500. g of nitrobenzene,
CH,NO₂, freezes at 3.2°C. Pure nitrobenzene freezes at 6.0°C. The molal freezing point constant
of nitrobenzene is _ °C/m.
a)
2.8
b)
3.2
c)
5.6
d)
7.0
e)
14.0
Below is the SN1 reaction of (S)-3-chlorocyclohexene and hydroxide ("OH). Draw the missing curved arrows, lone pairs of electrons, and nonzero
formal charges. In the third box, draw the two enantiomeric products that will be produced.
2nd attempt
Please draw all four bonds at chiral centers.
0
D
Draw the missing curved arrow notation. Add lone pairs of electrons and nonzero formal charges.
+ 노
V 1st attempt
Feedback
Please draw all four bonds at chiral centers.
See Periodic Table See Hint
F
P
41
H
Br
See Periodic Table
See Hint
H
L
How close are the Mulliken and Pauling electronegativity scales? (a) Now that the ionization energies and electron affinities have been defined, calculate the Mulliken and Pauling electronegativities for C, N, O and F. Compare them. (Make the necessary adjustments to the values, such as dividing the ionization energies and electron affinities by 230kj/mol) (b) Plot both sets of electronegativities against atomic number (use the same graph). (c) Which scale depends most consistently on position in the Periodic Table?
Chapter 19 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
Ch. 19.1 - Prob. 1PCh. 19.4 - Prob. 2PCh. 19.5 - Prob. 3PCh. 19.6 - Problem 19.6 What is the most acidic neutral...Ch. 19.7 - Problem 19.6 Write an ionic equation for the...Ch. 19.9 - Prob. 6PCh. 19.11 - Prob. 7PCh. 19.12 - Prob. 8PCh. 19.14 - Prob. 9PCh. 19.15 - Prob. 10P
Ch. 19.16 - Prob. 11PCh. 19.16 - Prob. 12PCh. 19 - Prob. 13PCh. 19 - Prob. 14PCh. 19 - Prob. 15PCh. 19 - Prob. 16PCh. 19 - Show how butanoic acid may be converted to each of...Ch. 19 - Show by a series of equations how could synthesize...Ch. 19 - Prob. 19PCh. 19 - Prob. 20PCh. 19 - Prob. 21PCh. 19 - Give the product of the reaction of pentanoic acid...Ch. 19 - Prob. 23PCh. 19 - Prob. 24PCh. 19 - Each of the follwing reactions has been reported...Ch. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - Prob. 28PCh. 19 - Prob. 29PCh. 19 - Prob. 30PCh. 19 - The 1H NMR spectra of formic acid (HCO2H), maleic...Ch. 19 - Prob. 32PCh. 19 - Prob. 33PCh. 19 - Prob. 34DSPCh. 19 - Prob. 35DSPCh. 19 - Lactonization Methods In Section we saw that...Ch. 19 - Prob. 37DSP
Knowledge Booster
Similar questions
- Below is the SN2 reaction between 2-bromopropane and iodide (I). Draw the mechanism arrows in the first box to reflect electron movements. In both boxes, add lone pairs of electrons and nonzero formal charges. 4th attempt Feedback 3rd attempt Feedback 1 -Br H :Bri :Br: ili See Periodic Table See Hint ini See Periodic Table See Hintarrow_forwardWhen 4-chloro-1-butanol is placed in sodium hydride, a cyclization reaction occurs. 3rd attempt 2 HO NaH CI D Draw the curved arrow notation to form the intermediate. 4 2 H₂ See Periodic Table See Hint =arrow_forwardSketch, qualitatively, the potential energy curves of the N-N bond of N2H4, N2 and N3- graph. Explain why the energy at the minimum of each curve is not the same.arrow_forward
- (a) Show that the lattice energies are inversely proportional to the distance between ions in MX (M = alkali metal, X = halide ions) by plotting the lattice energies of KF, KCl, and KI against the internuclear distances, dMX. The lattice energies of KF, KCl, and KI are 826, 717, and 645 kJ/mol, respectively. Does the correlation obtained correlate well? You will need to use a standard graphing program to construct the graph (such as a spreadsheet program). It will generate an equation for the line and calculate a correlation coefficient. (b) Estimate the lattice energy of KBr from your graph. (c) Find an experimental value for the lattice energy of KBr in the literature, and compare this value with the one calculated in (b). Do they agree?arrow_forwardShow the curved arrow mechanism and both products for the reaction between methyl iodide and propoxide. 1st attempt NV H 10: H H 1 Add the missing curved arrow notation. H + See Periodic Tablearrow_forwardFirst I wanted to see if you would mind checking my graphs behind me. (They haven't been coming out right)? Second, could you help me explain if the rate of reaction is proportional to iodide and persulfate of each graph. I highlighted my answer and understanding but I'm not sure if I'm on the right track. Thank you in advance.arrow_forward
- The heat of combustion for ethane, C2H6C2H6 , is 47.8 kJ/g. How much heat is produced if 1.65 moles of ethane undergo complete combustion?arrow_forwardReview of this week's reaction: H2NCN (cyanamide) + CH3NHCH2COOH (sarcosine) + NaCl, NH4OH, H2O ----> H2NC(=NH)N(CH3)CH2COOH (creatine) Q7. Draw by hand the reaction of creatine synthesis listed above using line structures without showing the Cs and some of the Hs, but include the lone pairs of electrons wherever they apply. (4 pts) Q8. Considering the Zwitterion form of an amino acid, draw the Zwitterion form of Creatine. (2 pts) Q9. Explain with drawing why the C—N bond shown in creatine structure below can or cannot rotate. (3 pts)arrow_forwardWould the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.arrow_forward
- Please help me answer a. Please and thank you I advance.arrow_forwardDraw both of the chair flips for both the cis and trans isomers for the following compounds: 1,4-diethylcyclohexane 1-methyl-3-secbutylcyclohexanearrow_forwardPpplllleeeaaasssseeee hellppp wiithhh thisss physical chemistryyyyy I talked like this because AI is very annoyingarrow_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 LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning


Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning

Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning

Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning