Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 1, Problem 38P
Interpretation Introduction
Interpretation: Structural formulas for at least three constitutional isomers with molecular formula
Concept introduction:
Compounds having different structures but the same molecular formula are known as isomers.
Structural isomerism or constitutional isomerism is shown by different compounds having difference in the sequence of their atoms but the same molecular formula.
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Given below are condensed structural formulas derived from the same molecular formula (C,H14). Identify which pair represents structural isomers,
that is, different molecules.
CH3
CH3
CH, CH3
CH, CH, CH-CH3
CH, CH-CH-CH3
CH3
CH, CH-CH,-CH2
CH3
CH, CH-CH CH,
CH3
CH3
A and C
O Cand D
O Band D
O D and A
Consider each pair of structures below. Indicate the isomeric relationship between each pair. Your choices are (i) identical structures (ii) constitutional isomers, (iii) conformational isomers, (iv) configurational isomers or (v) resonance structures.
Here is the chemical structure of 2-bromobutane:
H
H.
H
C-C-H
H :Br: H H
Decide whether each molecule in the table below is another molecule of 2-bromobutane, a molecule of an isomer of 2-bromobutane, or a molecule of an entirely
different compound.
molecule
relationship to 2-bromobutane
CH,
(Choose one)
H,c=ċ=CH,-Br
Explanation
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Chapter 1 Solutions
Organic Chemistry
Ch. 1 - Prob. 1PPCh. 1 - Prob. 2PPCh. 1 - Prob. 3PPCh. 1 - Prob. 4PPCh. 1 - Prob. 5PPCh. 1 - Prob. 6PPCh. 1 - Prob. 7PPCh. 1 - Prob. 8PPCh. 1 - Prob. 9PPCh. 1 - Prob. 10PP
Ch. 1 - Prob. 11PPCh. 1 - Prob. 12PPCh. 1 - Prob. 13PPCh. 1 - Prob. 14PPCh. 1 - Prob. 15PPCh. 1 - Prob. 16PPCh. 1 - Prob. 17PPCh. 1 - Prob. 18PPCh. 1 - Prob. 19PPCh. 1 - Prob. 20PPCh. 1 - Prob. 21PPCh. 1 - Practice Problem 1.22 Which of the following...Ch. 1 - Prob. 23PPCh. 1 - Prob. 24PPCh. 1 - Practice Problem 1.25
What do the bond angles of...Ch. 1 - Prob. 26PPCh. 1 - Practice Problem 1.27
Use VSEPR theory to predict...Ch. 1 - Practice Problem 1.28 Predict the bond angles of...Ch. 1 - 1.29 Which of the following ions possess the...Ch. 1 - 1.30 Write a Lewis structure for each of the...Ch. 1 - Prob. 31PCh. 1 - Add any unshared electrons to give each element an...Ch. 1 - Prob. 33PCh. 1 - What is the molecular formula for each of the...Ch. 1 - Prob. 35PCh. 1 - Prob. 36PCh. 1 - 1.37 Write bond-line formulas for all of the...Ch. 1 - Prob. 38PCh. 1 - Prob. 39PCh. 1 - Prob. 40PCh. 1 - Prob. 41PCh. 1 - (a) Cyanic acid (HOCN) and isocyanic acid (HN=C=O)...Ch. 1 - Consider a chemical species (either a molecule or...Ch. 1 - 1.44 Consider a chemical species like the one in...Ch. 1 - 1.45 Consider another chemical species like the...Ch. 1 - Draw a three-dimensional orbital representation...Ch. 1 - Ozone (O3) is found in the upper atmosphere where...Ch. 1 - Write resonance structures for the azide ion, N3....Ch. 1 - Write structural formulas of the type indicated:...Ch. 1 - Prob. 50PCh. 1 - 1.51 In Chapter 15 we shall learn how the...Ch. 1 - Prob. 52PCh. 1 - (a) Consider a carbon atom in its ground state....Ch. 1 - Open computer molecular models for dimethyl ether,...Ch. 1 - Boron is a group IIIA element. Open the molecular...Ch. 1 - 1.56 There are two contributing resonance...Ch. 1 - Prob. 1LGPCh. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Consider the compound with the following condensed...Ch. 1 - Prob. 7LGPCh. 1 - Prob. 8LGP
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- Given the following set of atoms, write a bond-line formula for a possible constitutional isomer for the compound. Show all formal charges and lone pairs. C atoms H atoms Other 3 1N atom and 10 atom (not on same C)arrow_forwardWrite structural formulas for some of the constitutional isomers of molecular formula C2H4NCl listed. All of these isomers contain only single bonds.arrow_forwardIn the following Lewis structure of [(CH3)2OH]*, every atom, bond and lone pair is positioned. To complete the structure, drag the formal charge tags to the appropriate atom(s). Each marker may be used more than once, or not at all. If an atom has a formal charge of zero, do not drag a tag to it. When you drag the marker in, place the little crosshairs in the upper left corner of the marker directly over the atom(s) in question (not above them). H. H-C Н-С-О-С-Н C-H H HH 2- II 2-arrow_forward
- Provide the bond line structures for four constitutional isomers with the molecular formula C9H13NOCl2 by following the directions shown below. Isomer #1: contains a tertiary alcohol and a secondary amine Isomer #2: contains an amide Isomer #3: contains a primary alkyl halide and a ketone Isomer #4: contains a cis alkene and a trans alkenearrow_forwardOctane has several isomers. Which of the following condensed formulas is NOT an isomer of octane? (You may select more than one. Incorrect answers will be penalised.) (C3H7)2CCH3 (C₂H5)2CHCH(CH3)2 (C₂H5)2CHC3H7 (C2H5)3CHCH3arrow_forwardSpecify the number of unshared pairs of electrons necessary to complete the valence shell of the labeled atoms, a-c in the following structures. Specify "0" if no pair of electron and that the atoms are NOT labeled in sequence. needs to be added. Notice that formal charges are indicated by or 1. 2. ob d a de C H H H a a b C b ✓Carrow_forward
- Draw all of the resonance structures for each of the following species. Be sure to include the curved arrows that indicate which pairs of electrons are shifted in going from one resonance structure to the next. Draw the resonance hybrid of each species. (a) ОН (b) (c) H3Carrow_forwardIn the following Lewis structure of [(CH3)2OH]+, every atom, bond and lone pair is positioned. To complete the structure, drag the formal charge tags to the appropriate atom(s). Each marker may be used more than once, or not at all. If an atom has a formal charge of zero, do not drag a tag to it. When you drag the marker in, place the little crosshairs in the upper left corner of the marker directly over the atom(s) in question (not above them). H H-C-O-C-H HHH - H I Η Η Η 0 0 + 2+ 2-arrow_forwardWhat is the formal charge (if any) of the carboxyl carbon (i.e., the one that is part of the carboxylic acid functional group) in the molecule (or ion) shown below? Assume all lone pairs of electrons are shown. H₂N- +2 -2 +1 -1 3 +3 O O :N: :N N: HO: : NO : NH₂ Ö: OHarrow_forward
- 7. The following six compounds have a molecular formula of C5H₁0O. Give the relationship of each pair of molecules. Your options are geometric isomers, constitutional isomers, or the same molecule. H3C-O H3C A A and B: B and C: B and F: D and E: F and A: CH3 H3C-O H3C CH3 C CH3 H3C CH3 OH CH3 E CH3 H3C CH3 H3C Farrow_forwardExample: Write the structural formulas for all the constitutional isomers that have the following molecular formula. a) C₂H7N b) C3H8Oarrow_forwardQ. 9a) Provide additional resonance structures for the following species. Remember to show lone pairs & formal charges where applicable + [ :N=N-F: +→ [:0-C!-O: → Q. 9b) Draw the Lewis Structure for NCCH2CO2NHCH3, determine the number of sigma bonds & the number of pi bonds present, and indicate the bond angle value around each carbon atom, each nitrogen atom, and each oxygen atom.arrow_forward
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