a)
Interpretation:
A structure for ketone or aldehyde with the following descriptions is to be proposed.
C4H7ClO, IR: 1715 cm-1; 1HNMR: 1.62 δ (Rel.area=3.00), 2.33 δ (Rel.area=3.00), 4.32δ (Rel.area=1.00).
Concept introduction:
In 1HNMR the aldehyde protons absorb near 10 δ with a coupling constant , J = 3Hz. Hydrogens on the carbon next to aldehyde group absorb near 2.0-2.3 δ. Methyl ketones show a sharp three proton singlet near 2.1 δ.
To purpose:
A structure for ketone or aldehyde with the following descriptions.
C4H7ClO, IR: 1715 cm-1; 1HNMR: 1.62 δ (Rel.area=3.00), 2.33 δ (Rel.area=3.00), 4.32δ (Rel.area=1.00).
b)
Interpretation:
A structure for ketone or aldehyde with the following descriptions is to be proposed.
C7H14O, IR: 1710 cm-1; 1HNMR: 1.02 δ (Rel.area=4.50), 2.12 δ (Rel.area=1.50), 2.33δ (Rel.area=1.00).
Concept introduction:
Aldehydes and ketones show a strong absorption band in IR from 1660-1770 cm-1. Aldehydes show two characteristic C-H absorptions between 2700-2760 cm-1 and 2800-2860 cm-1. Saturated aldehydes absorb near 1730 cm-1 while aromatic aldehydes and α, β- unsaturated aldehydes absorb near 1705 cm-1. Saturated ketones and cyclohexanones absorb near 1715 cm-1 while aromatic ketones and α, β- unsaturated ketones absorb near 1685-1690 cm-1. Cyclopentanones absorb around 1750 cm-1.
In 1HNMR the aldehyde protons absorb near 10 δ with a coupling constant , J = 3Hz. Hydrogens on the carbon next to aldehyde group absorb near 2.0-2.3 δ. Methyl ketones show a sharp three proton singlet near 2.1 δ.
To purpose:
A structure for ketone or aldehyde with the following descriptions.
C7H14O, IR: 1710 cm-1; 1HNMR: 1.02 δ (Rel.area=4.50), 2.12 δ (Rel.area=1.50), 2.33δ (Rel.area=1.00).
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Chapter 19 Solutions
ORGANIC CHEMISTRY W/OWL
- B 1 of 2 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 Brarrow_forwardThe number of 2sp^2 hybridized atoms in is: A. 8; B. 6; C.4; D.2; E.0;arrow_forwardThe highest boiling compound from among the following isA. 2-methylheptane; B. 3-methylheptane; C. 2,2-dimethylhexane;D. octane; E. 2,2,3-trimethylpentanearrow_forward
- Which 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_forwardWhich 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_forward
- Predict 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_forwardThe 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_forward
- Q5: 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_forwardcan you help me solve thisarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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