Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 6, Problem 6PP
PRACTICE PROBLEM 6.6
(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.]
(b) When enantiomerically pure (+)-2-chlorobutanc is allowed to react with potassium iodide in acetone in an
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• 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?
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)
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
ŚCH3
Chapter 6 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
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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- • 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_forwardName each alkene and specify its configuration by the E,Z system. (Be sure to indicate double bond stereochemistry using (E)/(Z) notation. It is not necessary to use italics in writing compound names.) (a) (b) (C) کو C1- Br لولهarrow_forward6.26 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 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_forward4.2 10 Give the reaction mechanism showing all possible products for the following reactions: (a) Reaction of 1-propene with hydrogen bromide, HBr (g) (b) Reaction of ethene with bromine, Br₂ (1)arrow_forwardO 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)arrow_forward
- 7.44 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_forward6.20 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 thearrow_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_forward
- 6.51b Explain the observed stereochemistry. When the second intermediate is redrawn from the following perspective, it becomes clear that O the electrons in the carbon-carbon-bond come from above the carbon-axygen x bond, allowing for the chirality center to be generated with the stereochemistry shown. the electrons in the carbon-carbon-bond come from below the carbon-oxygen x bond, allowing for the chirality center to be generated with the stereochemistry shown. the electrons in the carbon-exygen-bond come from below the carbon-cartion a bond, allowing for the chirality center to be generated with the stereochemistry shown. the electrons in the carbon-exygen x-band come from above the carbon-carbon bond, allowing for the chirality center to be generated with the stereochemistry shown. OOarrow_forwardConsider the reaction between (1S,3S)‑1‑chloro‑3‑methylcyclopentane and methanethiol in the presence of sodium hydroxide. (a) Draw the organic product and clearly indicate stereochemistry by showing the hydrogen on the chirality centers and using wedge and dash bonds. (b) Then analyze the stereochemistry of the product. racemic chiral achiral (1R, 3S) (1R, 3R) (1S, 3S)arrow_forward7.1 Provide the line structures of the products formed in the following reactions. One block may represent more than one product. (a) HBr Diethyl ether (b) H,0, H*arrow_forward
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