Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 6, Problem 7PP
PRACTICE PROBLEM 6.7
Rank the following carbocations in order of increasing stability:
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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
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)
PRACTICE PROBLEM 8.20
Specify the alkene and reagents needed to synthesize each of the following diols.
OH
HO-
(a)
(b)
(c)
HO.
н он
HO
(racemic)
(racemic)
Chapter 6 Solutions
Organic Chemistry
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 - Which SN1 reaction of each pair would you expect...Ch. 6 - Prob. 23PCh. 6 - Prob. 24PCh. 6 - Listed below are several hypothetical nucleophilic...Ch. 6 - Prob. 28PCh. 6 - Write conformational structures for the...Ch. 6 - 6.28 Consider the reaction of with .
(a) Would...Ch. 6 - Prob. 33PCh. 6 - Prob. 34PCh. 6 - Prob. 35PCh. 6 - Prob. 36PCh. 6 - 1-Bromobicyclo[2, 2,1] heptane is extremely...Ch. 6 - When ethyl bromide reacts with potassium cyanide...Ch. 6 - Prob. 41PCh. 6 - Prob. 42PCh. 6 - When the alkyl bromides (listed here) were...Ch. 6 - Prob. 44PCh. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - Prob. 47PCh. 6 - 6.42 The reaction of chloroethane with water in...Ch. 6 - Prob. 49PCh. 6 - Prob. 50PCh. 6 - Prob. 51PCh. 6 - Prob. 52PCh. 6 - 1-Bromo[2.2.1] bicycloheptane is unreactive toward...Ch. 6 - Open the computer molecular model tided...Ch. 6 - Prob. 56PCh. 6 - Consider the solvolysis reaction of (1S,...Ch. 6 - 2. Consider the following sequence of reactions,...Ch. 6 - Prob. 26PCh. 6 - Your task is to prepare isopropyl methyl ether by...Ch. 6 - Prob. 29PCh. 6 - 6.53 cis-4-Bromocyclohexanol racemic C6H10O...Ch. 6 - Prob. 31PCh. 6 - Explain the following observations: When...Ch. 6 - Prob. 38PCh. 6 - Prob. 1QCh. 6 - Prob. 2QCh. 6 - 6.3 A kinetic study yielded the following reaction...Ch. 6 - Prob. 4QCh. 6 - 6.5 Supply the missing reactants, reagents,...Ch. 6 - Which SN2 reaction will occur most rapidly....Ch. 6 - 6.7 Provide three-dimensional structures for the...
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- 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_forward• PRACTICE PROBLEM 6.6 S 2 reactions that involve substitution at a chirality center can be used to relate the configuration of one molecule to another, because we know the SN2 reaction will occur with inversion. (a) Illustrate how this is true by assigning R,S configurations to the 2-chlorobutane enantiomers based on the following data. [The configuration of (-)-2-butanol is given in Section 5.8C.] HO- (+)-2-Chlorobutane (-)-2-Butanol SN2 [a]3 = +36.00 (Enantiomerically pure) [a] = -13.52 (Enantiomerically pure) noin (b) When enantiomerically pure (+)-2-chlorobutane is allowed to react with potassium iodide in acetone in an SN2 reaction, the 2-iodobutane that is produced has a minus optical rotation. What is the configuration of (-)-2-iodobutane? Of (+)-2-iodobutane?arrow_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_forward
- 4.1 9 (a) Define geometric isomerism (b) How does geometric isomerism occur in alkenes? (c) Draw the cis- and trans- geometric isomers (if they exist) of: (i) BrCH=CHBr (ii) CH,CH,CH=CHCH,CH, (iii) Br- CH₂ - CH₂ - Brarrow_forward(a) H. H. 6.44 Which of the following reactions will yield a racemic mixture of products? HCI HBr (a) (c) H2 H2 (b) (d) Pt Ptarrow_forwardRank by the stability of the alkene isomers. The most stable isomer is 1, while the least stable isomer is 5. (A) (B) (C) (D) (E)arrow_forward
- Starting 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• PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forward6.2 (-)-Cameroonanol has been isolated from the essential oil of Echinops giganteus (globe thistle) plants and it is associated with a strong woody fragrance. Its structure, includ- ing relative stereochemistry, was confirmed when it was made in the laboratory according to the sequence shown below.' Recall that a C=C bond is made up of one o bond and one 7 bond. These two bonds together have a combined BDE (bond dissociation energy) of 607 kJ/mol. Use this information to estimate the AH° for the conversion of compound 1 into compound 2. Br two steps H.. H HBr hv H (-Cameroonanolarrow_forward7.13 A proton (H+) from trifluoromethanesulfonic acid, CF3SO2OH, can add to the alkyne shown here to yield two different carbocation products. (a) Draw the mechanism for each of these steps, along with the corresponding products. (b) Which carbocation is more stable? H3C H₂ IU C-C=CH + H-OSO₂CF3 H₂ ?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_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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