EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 9780100659469
Author: Bruice
Publisher: YUZU
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Chapter 4, Problem 69P
Chloramphenicol is a broad-spectrum antibiotic that is particularly useful against typhoid fever. What is the configuration of each of the asymmetric centers?
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Additional problems in preparation to Midterm #1:
1.) How can the following compounds be prepared using Diels-Alder reaction:
CH3 O
CN
(a)
(b)
CN
CH3
2.) What is the missing reagent in the shown reaction?
H3C
+ ?
H3C
H3C
CN
H3C
''CN
(၁)
H
3.) Write the products 1,2-addition and 1,4-addition of DBr to 1,3-cyclohexadiene.
Remember, D is deuterium, a heavy isotope of hydrogen. It reacts exactly like hydrogen.
4.) In the shown reaction, which will be the kinetic product and which will be the
thermodynamic product?
H3C
CI
H3C
HCI
H3C
+
5.) Which of the following molecules is aromatic?
(a)
(b)
(c)
H
6.) Which of the following molecules is aromatic?
(a)
(b)
(c)
7.) Write the mechanism for the shown reaction.
+
Ха
AICI 3
CI
8.) Suggest reagents that would convert benzene into the shown compounds.
CI
NO2
-8-6-6-8-a
(a)
(b)
(c)
(d)
(e)
(a)
SO3H
Br
The number of 2sp^2 hybridized atoms in is: A. 8; B. 6; C.4; D.2; E.0;
Chapter 4 Solutions
EBK ESSENTIAL ORGANIC CHEMISTRY
Ch. 4.1 - Draw the cis and trans isomers for the following:...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Prob. 6PCh. 4.2 - Prob. 7PCh. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Prob. 10PCh. 4.2 - Name each of the following:Ch. 4.2 - Draw the structure of (Z)-2,3-dimethyl-3-heptene.
Ch. 4.3 - Prob. 13PCh. 4.4 - Prob. 14PCh. 4.5 - Prob. 16PCh. 4.6 - Prob. 17PCh. 4.7 - Assign relative priorities to the groups or atoms...Ch. 4.7 - Name the following:Ch. 4.7 - Prob. 22PCh. 4.7 - Draw a perspective formula for each of the...Ch. 4.8 - Prob. 24PCh. 4.8 - Prob. 27PCh. 4.9 - Prob. 28PCh. 4.9 - Prob. 29PCh. 4.9 - Prob. 30PCh. 4.10 - Prob. 31PCh. 4.10 - Prob. 32PCh. 4.10 - Prob. 33PCh. 4.11 - Prob. 34PCh. 4.11 - a. Draw the stereoisomers of...Ch. 4.11 - Prob. 37PCh. 4.11 - Prob. 38PCh. 4.12 - Which of the following compounds has a...Ch. 4.12 - Draw all the stereoisomers for each of the...Ch. 4.12 - Limonene exists as two different stereoisomers....Ch. 4 - a. Draw three constitutional isomers with...Ch. 4 - Which of the following have an asymmetric center?...Ch. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Of all the possible cyclooctanes that have one...Ch. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Draw the stereoisomers of 2,4-dichlorohexane....Ch. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Prob. 62PCh. 4 - Draw structures for each of the following: a....Ch. 4 - Prob. 64PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Chloramphenicol is a broad-spectrum antibiotic...
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- The highest boiling compound from among the following isA. 2-methylheptane; B. 3-methylheptane; C. 2,2-dimethylhexane;D. octane; E. 2,2,3-trimethylpentanearrow_forwardWhich of the following features are found in the most stable structure ofCH5NO that does not have a CO bond?w. a π bond, x. two NH bonds, y. one OH bond, z. 3 lone pairsA. w, x; B. x, y; C. y, z; D. x, y, z; E. all of them.arrow_forwardWhich one of the following functional groups is not present in thecompound shownA. amine; B. aldehyde, C. ether; D. amide. E. ketonearrow_forward
- Which of the following formulas correspond to at least one compound inwhich resonance is important?w. C2H5N x. C3H5Br; y. C3H4; z. C4H6.A. w, x, y; B. x, y, z; C. w, x, z; D. w, y, z; E. all of themarrow_forwardPredict the product(s) that are formed after each step for reactions 1-4. In each case, consider formation of any chiral center(s) and draw all expected stereoisomers. 1) OH 1) HBr (SN2) 2) NaOH, heat 3) BH3, THF 4) H2O2, NaOH 2) OH 1) SOCI 2, py 2) NaOEt 3) Br2, H₂O 3) OH 1) H2SO4 conc. 2) HBr, ROOR 3) KOtBu 4) OH 1) TsCl, py 2) NaOEt 3) 03 4) DMSarrow_forwardWhich of the following rings has the least strain in its most stableconformation?A. Cyclobutane; B. Cyclopentane; C. Cyclohexane; D. Cycloheptane;E. Cyclooctanearrow_forward
- The number of different carbon skeletons that have a main chain of 9carbons and an ethyl branch isA 3; B. 4; C. 5; D. 6; E. 7arrow_forwardQ5: Classify the following pair of molecules as constitutional isomers, enantiomers, diastereomers, the same molecule, or completely different molecules. Br O CI Br OH OH 111 Br .!!!/Br F OH and ...m Br Br OH CI Br OH ་་་་་" ། ་arrow_forwardConsidering only rotation around the 1-2 bond, how many differentstaggered conformations are there of 1,2-dibromo-1,2-dichloropropane?A: 2; B. 3; C. 4; D. 6; E. more than 6.arrow_forward
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