Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 11, Problem 24PP
Interpretation Introduction
Interpretation:
The structures for
Concept introduction:
The crown ethers are named as
Here,
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Explain why
(i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride.
(ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.
(i)
increasing solubility in water.
(CH3),CHCH,OH
CH;CH,CH,CH,OH
CH;CH,CH,Br
CH;CH,OCH3
(a)
(b)
(c)
(d)
least soluble
most soluble
(ii)
increasing stability.
CH
-CH3
H3C
-CH3
H3C
-CH3
H3C.
-CH3
(а)
(b)
(c)
(d)
least stable
stable
(iii)
increasing stability.
CH,CH3
CH3
CH,CH3
CH,CH3
CH,CH3
CH3
-CH3
`CH3 (CH3),CH´
(CH3),CH'
`CH3 (CH3),CH´
`CH
`CH3 (CH3),CH´
CH3
(d)
(a)
(b)
(c)
least stable
most stable
(iv)
increasing boiling point.
(CH3),COH
(CH3),CHCH,NH,
(CH3),CHCH,OH
(CH3),NCH,CH3
(a)
(b)
(c)
(d)
lowest bp
highest bp
2. (a) Provide the IUPAC name for the following molecules (A) to (C). In your answer,
include a description of how the name was derived.
Te
(A)
(8)
(D)
(b) Consider the three compounds, (D), (E), and (F) below.
مام
(E)
(C)
(F)
-OH
(i)
State the hybridization of all the carbon atoms in compound (F).
(ii)
With the aid of diagrams, explain how (D) and (E) are stabilised, and explain
why (F) is the least stable carbocation.
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Prob. 1PPCh. 11 - Practice Problem 11.2 Give bond-line formulas and...Ch. 11 - Prob. 3PPCh. 11 - Prob. 4PPCh. 11 - Prob. 5PPCh. 11 - Prob. 6PPCh. 11 - Prob. 7PPCh. 11 - Practice Problem 11.8 Show how you would prepare...Ch. 11 - Prob. 9PPCh. 11 - Prob. 10PP
Ch. 11 - Practice Problem 11.11
An exception to what is...Ch. 11 - Prob. 12PPCh. 11 - Prob. 13PPCh. 11 - Prob. 14PPCh. 11 - Prob. 15PPCh. 11 - Prob. 16PPCh. 11 - Prob. 17PPCh. 11 - Prob. 18PPCh. 11 - Practice Problem 11.19
Propose structures for each...Ch. 11 - Prob. 20PPCh. 11 - Prob. 21PPCh. 11 - Prob. 22PPCh. 11 - Prob. 23PPCh. 11 - Prob. 24PPCh. 11 - Give an IUPAC substitutive name for each of the...Ch. 11 - Prob. 26PCh. 11 - Prob. 27PCh. 11 - Prob. 28PCh. 11 - Prob. 29PCh. 11 - 11.30. Show how you might prepare 2-bromobutane...Ch. 11 - Prob. 31PCh. 11 - Prob. 32PCh. 11 - Prob. 33PCh. 11 - Considering A-L to represent the major products...Ch. 11 - Write structures for the products that would be...Ch. 11 - Prob. 36PCh. 11 - Provide the reagents necessary for the following...Ch. 11 - 11.38. Predict the major product from each of the...Ch. 11 - Predict the products from each of the following...Ch. 11 - Provide the reagents necessary to accomplish the...Ch. 11 - 11.41. Provide reagents that would accomplish the...Ch. 11 - Prob. 42PCh. 11 - 11.43. A synthesis of the -receptor blocker called...Ch. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - 11.46. For each of the following, write a...Ch. 11 - 11.47. Vicinal halo alcohols (halohydrins) can be...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Prob. 51PCh. 11 - Prob. 52PCh. 11 - Outlined below is a synthesis of the gypsy moth...Ch. 11 - Prob. 54PCh. 11 - Prob. 55PCh. 11 - Prob. 56PCh. 11 - 11.57. When the 3-bromo-2-butanol with the...Ch. 11 - 11.58. Reaction of an alcohol with thionyl...Ch. 11 - Prob. 59PCh. 11 - Prob. 60PCh. 11 - Prob. 1LGPCh. 11 - Prob. 2LGPCh. 11 - Synthesize the compound shown below from...
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- 2) Application of the polygon-and-circle technique (Frost circle) reveals that single electrons occupy each of the two nonbonding orbitals in the molecular orbital diagram of: A) Cyclobutadiene B) Benzene C) Cyclopropenyl cation D) Cyclopentadienyl anionarrow_forwardC. Which of the following chemical formula/structure will have a greater melting point? Encircle your answer. 1. (a) CH3(CH2)14CO2H (b) CH3(CH2) 10CO2H 2. (a) (Z)-CH3(CH2)5CH= CH(CH2)7CO2H (b) CH3(CH2)14CO2Harrow_forward4. Octatetraene, C8H10, is an 8-membered linear carbon chain with alternating single and double bonds. As a result, each carbon is left with an unhybridized p-orbital containing one electron. This problem will take you through steps to construct and fill the molecular orbital diagram for octatetraene based on the way these different p-orbitals can come together. a) The various molecular orbitals formed from octatetraene’s 8 unhybridized p-orbitals are shown on the next page. Draw the nodal planes for each molecular orbital. Hint: A nodal plane is a line through the molecule that denotes the sites of destructive interference. An example is shown below with ethylene. b) Based on the nodal planes, arrange the energy levels corresponding to the 8 molecular orbitals on the energy level diagram (label them using the numbering provided on the left side of the molecular orbitals) on the next page, in order of lowest to highest energy. c) Populate your molecular…arrow_forward
- Square planar molecules with formula AB2C2 and octahedral molecules with formulas AB4C2 and AB3C3 feature diastereoisomers. Recall that trigonal bipyramidal geometry features two distinct positions: axial and equatorial. Draw all diastereoisomers for trigonal bipyramidal molecules with formula (a) AB4C and (b) AB3C2. You must indicate the stereochemistry using full and dashed wedges and label all positions as either axial (ax) and equatorial (eq)..arrow_forwardWrite structural formulas for toluene (C6H5CH3) and for benzoic acid (C6H5CO2H) (a) as resonance hybrids of two Kekulé forms and (b) with the Robinson symbol.arrow_forwardCompare Structure I below with Structures A, B, and C and match each structure with the correct relationship they have with Structure I.arrow_forward
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