EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Chapter 7, Problem 102IP
(a)
Interpretation Introduction
Interpretation:
A mechanism for the conversion of 1 to 2b must be drawn.
Concept Introduction :
Triphenylmethyl carbocation is a very stable carbocation due to resonance stabilization with three benzene rings.
(b)
Interpretation Introduction
Interpretation:
Conversion of compound 1 to 2 (2a, 2b and 2c) is instantaneous in all the cases must be explained.
Concept Introduction :
Rate determining step for SN1 reaction is the carbocation formation step. It is slowest step. Next step is rapid attack of the nucleophile to the carbocation.
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One of the molecules shown can be made using the Williamson ether synthesis. Identify the ether and draw the
starting materials.
A
B
C
Strategy: Review the reagents, mechanism and steps of the Williamson ether synthesis. Determine which of the molecules can
be made using the steps. Then analyze the two possible disconnection strategies and deduce the starting materials. Identify the
superior route.
Two possible bonds can be formed to make ether C. The highlighted bond in each structure indicates the bond formed in each
route. Let's consider each route and determine which is ideal.
O
Yo
C-option1
C-option2
Consider option 1. Draw the alkyl bromide and alkoxide that would give option 1.
Select
Draw
Rings
More
Erase
C H Br 0
Will these reagents give an efficient Williamson ether synthesis?
yes
no
O
Decide on the mechanism for each substitution, and then pick the solvent that affords the faster reaction.
a.(CH3CH2)2CClCH3 + CH3OH in CH3OH or DMSO
b.CH3CH2CH2Br + −OH in H2O or
c. DMF (CH3CH2)2CHCl + CH3O− in CH3OH or HMPA
A student wanted to know whether the greater proximity of the ucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl.Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?
Chapter 7 Solutions
EBK ORGANIC CHEMISTRY-PRINT COMPANION (
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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- A student wanted to know whether the greater proximity of the nucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl. Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?arrow_forward6. Draw the kinetic and thermodynamic enolates formed when 3-methylbutan-2-one (aka methyl isopropyl ketone) is treated with a base (Na OCH), for example). Please make sure to draw the oxide form, not the carbanion form. ( Kinetically controlled LDA 3-methylbutan-2-one Na* OCH₂ Thermodynamically controlled enolatearrow_forward3. Explain the regioselectivity of the nucleophilic attack of the chloronium ion below. Compare it to nucleophilic attack of an epoxide. H₂C Десня CH₂ Nuc: Nuc:arrow_forward
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