Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 8, Problem 7PP
Interpretation Introduction
Interpretation:
The given
Concept introduction:
A reaction in which water molecule is added to an unsaturated compound is called an acid catalyzed hydration.
The order of stability of carbocation highly depends on the number of hyperconjugable hydrogen atoms. Higher the numbers higher is the stability. Among them tertiary carbocation is most stable, the primary carbocation is least stable and the secondary carbocation lies between primary and tertiary carbocation.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
+
H3C- CH₂ - CH2 - COR and
have undergone
McLafferty rearrangement and
Ortho effect respectively. What
are the possible fragments
obtained as a result of these
processes ?
COOCH3
OH
+
(A) [R-CH₂-C
(A) R-CH₂-CH₂ - CH₂ - COH
@E
OH]: [c
C6H4 O and CO
(B) H₂C=CROH and H₂C = CH₂
[2] : [ C₂H4O3 and CH4
(C)
(D) H₂CCROH and C₂H4; [(C6H4O), CO and CH₂OH]
RH, C₂H4 and CH₂CO; [(C₂H4O), CO and CH₂OH]
(c) The structures of lycopene, beta-carotene and retinol are shown below.
Lycopene
Beta-carotene
H3C CH;
CH3
CH3
OH
Retinol (vitamin A)
CH3
Using appropriate reaction mechanisms:
(i)
Show how lycopene is converted into beta-carotene.
(ii)
Briefly explain how retinol is formed from beta-carotene.
The Claisen condensation of two molecules of ethyl phenylacetate (shown
below) in the presence of sodium ethoxide (NaOEt) leads to which of the
following products?
.CH3
C,H;CH,C-CH2C,H5
CGH5CH2C-O-ĈCH2C,H5
C6H5CH2C-CHCO,C,H5
C,H,CH,C-
-CH,CO,C,H5
Chapter 8 Solutions
Organic Chemistry
Ch. 8 - Prob. 1PPCh. 8 - PRACTICE PROBLEM Outline mechanisms for the...Ch. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - PRACTICE PROBLEM
8.5 In one industrial synthesis...Ch. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - PRACTICE PROBLEM (a) Outline a likely mechanism...
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - The reaction of bromine with cyclohexene involves...Ch. 8 - Prob. 43PCh. 8 - Internal alkynes can be isomerized to terminal...Ch. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 48PCh. 8 - 8.49 Farnesene (below) is a compound found in the...Ch. 8 - Prob. 50PCh. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 52PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Prob. 54PCh. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 59PCh. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 64PCh. 8 - Prob. 66PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - 8.65
(a)Based on the following information, draw...Ch. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGPCh. 8 - 8.1 A hydrocarbon whose molecular formula is...Ch. 8 - Prob. 2QCh. 8 - Give the major product of the reaction of...Ch. 8 - The compound shown here is best prepared by which...Ch. 8 - 8.5 A compound whose formula is C6H10 (Compound A)...Ch. 8 - Prob. 6QCh. 8 - 8.7 Which reaction sequence converts cyclohexene...Ch. 8 - Which of the following sequences leads to the best...
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
- 8. Plan syntheses of the following compounds. You may use the given starting material and any compound containing three or fewer carbons. (a) (b) (c) NH₂ sef= -OHarrow_forwardIn an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forwardShow how H may be converted into G and I. For both sequences, provide reagents and the structure and stereochemistry of any intermediate compounds.arrow_forward
- Devise a synthesis of (E)-tetradec-11-enal, a sex pheromone of the spruce budworm, a pest that destroys fir and spruce forests, from acetylene, Br(CH2)10OH, and any needed organic compounds or inorganic reagents.arrow_forward(a) (b) (c) 3. Complete the following reaction scheme. Give all product(s) and indicate major or minor and any relevant stereochemistry. (60 points-4 points each) Br Br Br OH heat heat NaCN DMSO 3arrow_forwardPart 6-(33-35) Predict the product or products of each of the following reactions: (а) CH-CH-ОH + HCOOН (b) н—С-С—CH, + H2 — (c) C2H5. `C=C `H H + HBr – H'arrow_forward
- Q1arrow_forward2-Give the structures, including stereochemistry of compounds A and B in the following sequence of reactions: OH O₂N- -SO₂Cl Pyridine Compound A LiBr Acetone -Compound Barrow_forwardIdentify the pericyclic reactions in the followingreaction schemes. Give the complete reaction name and indicate the course of the reaction with the aid of the arrow notation.arrow_forward
- Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardHow many Claisen condensation products are possible in the reaction of equal amounts of ethyl ethanoate (CH;CO2Et) and ethyl 2,2-dimethylpropanoate (CH;C(CH3)2CO2Et)? (a) only one (b) two (c) three (d) four (e) five (f) sixarrow_forwardThe reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion thanretention of configuration. Propose a mechanism that accounts for racemization with excess inversion.(b) Under the same conditions, an optically active sample of trans-2-bromocyclopentanol reacts with concentrated aqueous HBr to give an optically inactive product, (racemic) trans-1,2-dibromocyclopentane. Proposea mechanism to show how this reaction goes with apparently complete retention of configuration, yet withracemization. (Hint: Draw out the mechanism of the reaction of cyclopentene with Br2 in water to give thestarting material, trans-2- bromocyclopentanol. Consider how parts of this mechanism might be involved in thereaction with HBr.)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