ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Chapter 6.13B, Problem 6.24P
3-Bromocyclohexene is a secondary halide, and benzyl bromide is a primary halide Both halides undergo SN1 substitution about as fast as most tertiary halides Use resonance structures to explain this enhanced reactivity.
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The high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized
covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity
is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa
mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow
process). In the second step, the nucleophile attacks the carbocation from either side to form the product
(fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy
(bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction,
the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate
(transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a
configuration opposite to that of the…
Cinnamoyl chloride (C9H7CIOO) can be prepared by the two-step sequence shown below.
Reaction 1: C7H60 + CAH6O3 C9H8O2 + C2H402
Reaction 2: C9H&O2 + SOC2 → C9H7oci + sO2 + HCI
CH60 C4H6O3 C9H8O2 C2H402 SOCI2 C9H,Oci SO2
HCI
Molar masses
106.12 102.09
148.16
60.05
118.96
166.60
64.07 36.46
(in g mol-1)
What is the percent atom economy for the synthesis of cinnamoyl chloride? Enter an answer accurate to three
significant figures.
Number
Nucleophilic aromatic substitution involves the formation of a resonance-stabilized carbanion intermediate
called a Meisenheimer complex as the nucleophile attacks the ring carbon carrying the eventual leaving
group; electron-withdrawing groups ortho and/or para to the site of attack help to stabilize this structure
via resonance.
For the reaction below, draw the structure of the stabilized reaction intermediate in the box below.
CI
F3C
CF3
NO₂
F3C
N
CF3
NO₂
• You do not have to consider stereochemistry.
• Draw the Meisenheimer complex with a formal charge of 0 on the nucleophilic atom. If more than
one resonance structure is possible, only draw the most important one.
Chapter 6 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
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