ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
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Chapter 6, Problem 11PP
Interpretation Introduction
Interpretation:
The nucleophilic substitution reaction that can occur in the given four primary
Concept introduction:
In
In organic chemistry, the nucleophilic substitution that consists of bimolecular reaction, one-step mechanism, and there is no formation of a carbocation is known as
In an alkyl halide, the reaction takes place between halogen atoms and
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O PRACTICE PROBLEM 8.14
Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace-
tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled
compounds.s el en
olad lo nohibbs ad
CH3
(a) (CH3)2CHCH2CH,D
(b) (CH3),CHCHDCH3 (c)
(+ enantiomer)
(d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a
synthesis of the following?
hab erl
(+ enantiomer)he
imo
(nwond-ben)
CH3
H.
(asoholea)
6.20 Account for the regioselectivity and stereoselectivity observed when 1-methylcyclopentene
is treated with each reagent.
(a) BH,
(b) Br₂ in H₂O
(c) Hg(OAc), in H₂O
6.21 Draw a structural formula for an alkene with the indicated molecular formula that
ion product (more than one alkene may give the
6.17 Predict the organic product(s) of the reaction of 2-butene with each reagent.
(c) Cl₂
(a) H₂O (H₂SO₂)
(d) Br₂ in H₂O
(f) Cl₂ in H₂O
(g) Hg (OAc)2, H₂O
(b) Br
(e) HI
(h) product (g) + NaBH,
Chapter 6 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Ch. 6 - Prob. 1PPCh. 6 - Prob. 2PPCh. 6 - Prob. 3PPCh. 6 - Prob. 4PPCh. 6 - Prob. 5PPCh. 6 - PRACTICE PROBLEM 6.6
reactions that involve...Ch. 6 - PRACTICE PROBLEM 6.7 Rank the following...Ch. 6 - Prob. 8PPCh. 6 - Prob. 9PPCh. 6 - Prob. 10PP
Ch. 6 - Prob. 11PPCh. 6 - Prob. 12PPCh. 6 - Prob. 13PPCh. 6 - Prob. 14PPCh. 6 - Prob. 15PPCh. 6 - Prob. 16PPCh. 6 - Prob. 17PPCh. 6 - Prob. 18PPCh. 6 - Prob. 19PPCh. 6 - Prob. 20PCh. 6 - Prob. 21PCh. 6 - Prob. 22PCh. 6 - Prob. 23PCh. 6 - Prob. 24PCh. 6 - Listed below are several hypothetical nucleophilic...Ch. 6 - Prob. 26PCh. 6 - 6.27 Write conformational structures for the...Ch. 6 - 6.28 Consider the reaction of with .
(a) Would...Ch. 6 - Prob. 29PCh. 6 - Prob. 30PCh. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - 1-Bromobicyclo[2, 2,1] heptane is extremely...Ch. 6 - When ethyl bromide reacts with potassium cyanide...Ch. 6 - Prob. 35PCh. 6 - Prob. 36PCh. 6 - When the alkyl bromides (listed here) were...Ch. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41PCh. 6 - 6.42 The reaction of chloroethane with water in...Ch. 6 - Prob. 43PCh. 6 - Prob. 44PCh. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - 1-Bromo[2.2.1] bicycloheptane is unreactive toward...Ch. 6 - Open the computer molecular model tided...Ch. 6 - Prob. 49PCh. 6 - Consider the solvolysis reaction of (1S,...Ch. 6 - 2. Consider the following sequence of reactions,...
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Similar questions
- 6.26 There is an overall 29-fold difference in reactivity of 1-chlorohexane, 2-chlorohexane, and 3-chlorohexane toward potassium iodide in acetone. (a) Which one is the most reactive? Why? (b) Two of the isomers differ by only a factor of 2 in reactivity. Which two are these? Which one is the more reactive? Why?arrow_forward6.49 Reaction of 3,3-dimethyl-1-butene with hydrogen iodide yields two compounds A and B, each having the molecular formula C6H₁3I, in the ratio A:B = 90:10. Compound A, on being heated with potassium hydroxide in n-propyl alcohol, gives only 3,3-dimethyl-1-butene. Compound B undergoes elimination under these conditions to give 2,3-dimethyl-2-butene as the major prod- uct. Suggest structures for compounds A and B, and write a reasonable mechanism for the for- mation of each.arrow_forward7.44 Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination. (а) СH;CH—CH, (b) (CH3)2С—СH2 (c) BRCH=CB12 CH3 (d) CH3arrow_forward
- PRACTICE PROBLEM 6.5 Using chair conformational structures (SectionA), show the nueleophilie substitution reaction that would take place when trans-1-bromo-4-tert-butyleyclohexane reacts with lodide lon. (Show the most stable conformnation of the reactant and the product.) Sy2 reactions always occur with inversion of configurationarrow_forward• PRACTICE PROBLEM 8.12 Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed in reagent "disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The name "amyl" is an old common name for a five-carbon alkyl group.) donbyarrow_forward7.26 Predict the principal organic product of each of the following reactions. Specify stereochemistry where appropriate. ONa (a) (b) (c) (d) (e) (1) (g) (h) e (j) L OH (1) H- Br + + OH OCH3 Br Br CoHs ONa NaOH NaN3 dioxane-water Ao fo X A Br NH3 methanol HCI CHC13 -CH3 CH,SNa -H OOH (k) CH₂(CH₂)₁6CH₂OTS + CH3CH₂CH₂CH₂SNa → CGHS CH₂ONa CH3OH 1. LIAIH, diethyl ether 2. H₂O K₂CO3 acetonearrow_forward
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- 14.35 How could you use Diels-Alder reactions to prepare the following products? Show the starting diene and dienophile in each case. (a) H (b) H CN H (c) H H. H--arrow_forwardArrange the alkenes in each set in order of increasing rate of reaction with HI and explain the basis for your ranking. Draw the structural formula of the major product formed in each case. (a) and (b) H3CH₂CHC=CH₂ and (H3C) 2C=CHCH3arrow_forwardStarting with (S)-2-bromobutane, outline syntheses of each of the following compounds:• PRACTICE PROBLEM 6.19 (a) (R)-CH,CHCH,CH3 (c) (R)-CH,CHCH,CH3 OH bA-(2) ÓCH,CH3 SH muinolue for (b) (R)-CH,CHCH,CH3 (d) (R)-CH,CHCH,CH3 tho betallgo ÓCCH3 ŚCH3arrow_forward
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