ORGANIC CHEMISTRY LL PRINT UPGRADE
4th Edition
ISBN: 9781119810643
Author: Klein
Publisher: WILEY
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Chapter 7.3, Problem 6ATS
Interpretation Introduction
Interpretation: The synthesis of Aldingenin C involves the conversion of the compound to 2 via the intramolecular
Concept introduction:
A molecule can have both nucleophilic and electrophilic centers. An electrophilic center must be electron-deficient and can form a bond with a nucleophile. Here the nucleophile is an electron-rich species that can react with cation or any other electrophile. The
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4) Propose a synthetic pathway to prepare 2-methyl-propan-2-ol from propane.
You're allowed to use any reagents you like but all the carbon atoms in
your product should come from the propane.
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It must be propanone otherwise the conversion would be too long.
(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, andthe products. Note that the initial product is the salt of an amine (RNH3+ Br - ), which is deprotonated by the excess ammonia to give the amine.
CH3
Ph3P-CHCH3
H3C
H3C
Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to
an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine
oxide and an alkene.
Ph3P-CHCH3
H3C
The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as
butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene
:0:
CH3
Com
The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…
Chapter 7 Solutions
ORGANIC CHEMISTRY LL PRINT UPGRADE
Ch. 7.2 - Prob. 1CCCh. 7.3 - Prob. 2CCCh. 7.3 - Prob. 1LTSCh. 7.3 - Prob. 3PTSCh. 7.3 - Prob. 4ATSCh. 7.3 - Prob. 2LTSCh. 7.3 - Prob. 5PTSCh. 7.3 - Prob. 6ATSCh. 7.3 - Prob. 7CCCh. 7.4 - Prob. 8CC
Ch. 7.5 - Prob. 9CCCh. 7.6 - Prob. 10CCCh. 7.6 - Prob. 11CCCh. 7.7 - Prob. 12PTSCh. 7.7 - Prob. 13PTSCh. 7.7 - Prob. 14ATSCh. 7.7 - Prob. 4LTSCh. 7.7 - Prob. 16ATSCh. 7.7 - Prob. 17CCCh. 7.7 - Prob. 18CCCh. 7.7 - Prob. 5LTSCh. 7.7 - Prob. 19PTSCh. 7.7 - Prob. 20ATSCh. 7.8 - Prob. 21PTSCh. 7.8 - Prob. 22ATSCh. 7.8 - Prob. 23CCCh. 7.8 - Prob. 24CCCh. 7.8 - Prob. 25CCCh. 7.8 - Prob. 26CCCh. 7.8 - Prob. 27CCCh. 7.9 - Prob. 7LTSCh. 7.9 - Prob. 29ATSCh. 7.9 - Prob. 30ATSCh. 7.9 - Prob. 31ATSCh. 7.10 - Prob. 32CCCh. 7.10 - Prob. 33CCCh. 7.10 - Prob. 34CCCh. 7.11 - Prob. 8LTSCh. 7.11 - Prob. 35PTSCh. 7.11 - Prob. 36PTSCh. 7.11 - Prob. 37ATSCh. 7.11 - Prob. 9LTSCh. 7.11 - Prob. 40PTSCh. 7.11 - Prob. 41ATSCh. 7.12 - Prob. 42CCCh. 7.12 - Prob. 43CCCh. 7.12 - Prob. 44CCCh. 7.12 - Prob. 45CCCh. 7.12 - Prob. 46CCCh. 7 - Prob. 47PPCh. 7 - Prob. 48PPCh. 7 - Prob. 49PPCh. 7 - Prob. 50PPCh. 7 - Prob. 51PPCh. 7 - Prob. 52PPCh. 7 - Prob. 53PPCh. 7 - Prob. 54PPCh. 7 - Prob. 55PPCh. 7 - Prob. 56PPCh. 7 - Prob. 57PPCh. 7 - Prob. 58PPCh. 7 - Prob. 59PPCh. 7 - Prob. 60PPCh. 7 - Prob. 61PPCh. 7 - Prob. 64PPCh. 7 - Indicate whether you would use NaOEt or tBuOK to...Ch. 7 - Prob. 68PPCh. 7 - Draw a plausible mechanism for each of the...Ch. 7 - Prob. 70PPCh. 7 - Prob. 71PPCh. 7 - Prob. 72PPCh. 7 - Prob. 73PPCh. 7 - Prob. 74PPCh. 7 - Prob. 77PPCh. 7 - Prob. 78PPCh. 7 - Prob. 81ASPCh. 7 - Prob. 87ASPCh. 7 - Prob. 90ASPCh. 7 - Prob. 91IPCh. 7 - Prob. 92IPCh. 7 - Prob. 93IPCh. 7 - Prob. 94IPCh. 7 - Prob. 95IPCh. 7 - Prob. 96IPCh. 7 - Prob. 97IPCh. 7 - Prob. 98IPCh. 7 - Prob. 99IPCh. 7 - Prob. 100IPCh. 7 - Prob. 101IPCh. 7 - Prob. 102IPCh. 7 - Prob. 103IPCh. 7 - Prob. 105IPCh. 7 - Prob. 106IPCh. 7 - Prob. 107IPCh. 7 - Prob. 109IPCh. 7 - Prob. 110CPCh. 7 - Prob. 112CPCh. 7 - Prob. 114CP
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