Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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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
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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
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(asoholea)
Please don't provide handwritten solution ...
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 - 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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- Determine which carbocation rearrangements you drew for Problem 7.36 produce a significantly more stable carbocationthan the reactant.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• 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
- 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 the following alkenes in order of increasing stabilityarrow_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_forwardReview Problem 5.2 Construct handheld models of the 2-butanols represented in Fig. 5.3 and demonstrate for yourself that they are not mutually superposable. (a) Make similar models of 2-bromo- propane. Are they superposable? (b) Is a molecule of 2-bromopropane chiral? (c) Would you expect to find enantiomeric forms of 2-bromopropane? H но OH H HO HH OH OH HO H CH CH CH C CH CH II II (a) (b) (c) Figure 5.3 (a) Three-dimensional drawings of the 2-butanol enantiomers I and II. (b) Models of the 2-butanol enantiomers. (c) An unsuccessful attempt to superpose models of I and II.arrow_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_forward
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