Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 12A, Problem 18P
Propose two molecular formulas for each molecular ion: (a) 102; (b) 98; (c) 119; (d) 74
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Your chemistry professor draws a number of molecules on the board: (1) CH4 ; (2) H2C=CH2 ; (3) H2C=C=CH2 ; and (4) H2C=C=C=CH2. You muse about all the molecules that chemists draw on a two-dimensional board and wonder which ones are actually planar, existing basically as they appear on the board, and which ones are not plane but rather three-dimensional.
Answer ALL of the following questions.
What are the specific orbital overlaps (i.e., sp3-sp3) that are in each of the molecules?
What are the bond angles for each central atom in each molecule?
Which molecules are planar and which are non-planar?
Your chemistry professor draws a number of molecules on the board: (1) CH4 ; (2) H2C=CH2 ; (3) H2C=C=CH2 ; and (4) H2C=C=C=CH2. You muse about all the molecules that chemists draw on a two-dimensional board and wonder which ones are actually planar, existing basically as they appear on the board, and which ones are not plane but rather three-dimensional.
Answer the following questions.
What is the geometry and hybridization of the carbon in CH4?
What is the geometry and hybridization of each central carbon atom in the remaining molecules?
Draw each molecule showing the bonds and identify each bond in all the molecules as s or p.
What are the specific orbital overlaps (i.e., sp3-sp3) that are in each of the molecules?
What are the bond angles for each central atom in each molecule?
Which molecules are planar and which are non-planar?
1.57
Which compound in each of the following pairs would you expect to have the greater dipole
moment u? Why?
(a) HF or HCI
(b) HF or BF3
(c) (CH3)3CH or (CH3)3CCI
(d) CHCl3 or CCI F
(e) CH3NH₂ or CH₂OH
(f) CH3NH₂ or CH₂NO₂
Chapter 12A Solutions
Organic Chemistry (6th Edition)
Ch. 12A.1 - What is the mass of the molecular ion formed from...Ch. 12A.1 - Prob. 3PCh. 12A.2 - Prob. 6PCh. 12A.2 - What molecular ions would you expect for the...Ch. 12A.3 - The mass spectrum of 2,3-dimethylpentane also...Ch. 12A.3 - The base peak in the mass spectrum of 2, 2,...Ch. 12A - Problem-13.24 The mass spectrum of the following...Ch. 12A - Prob. 16PCh. 12A - Which compound gives a molecular ion at m/z= 122,...Ch. 12A - Propose two molecular formulas for each molecular...
Ch. 12A - Propose four possible structures for a hydrocarbon...Ch. 12A - Problem-13.29 What is the molecular formula for...Ch. 12A - Problem-13.30 Propose a molecular formula for rose...Ch. 12A - 13.31 Match each structure to its mass spectrum
Ch. 12A - 13.32 Propose two possible structures for a...
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- help with 2 (a-c)arrow_forward3. Use the symbols 6* and & to show the direction of the polarity of the indicated bond in H,C-OH. Use the symbois 6 and 6 to show the direction of the polarity of the indicated bond in each of the following compounds: (a) HO-H (b) F- Br (c) H,C- NH, (d) H,C-CI (e) HO - Br (1) H,C-Li (8) 1- CI (h) H,N - OHarrow_forward5. A molecule with the formula C,H is a(n): (a) hexane (b) propane (c) decane (d) butane (e) ethanearrow_forward
- Compound X, isolated from lanolin (sheep’s wool fat), has the pungent aroma of dirty sweat socks. A careful analysis showed that compound X contains 62.0% carbon and 10.4% hydrogen. No nitrogen or halogen was found.(a) Compute an empirical formula for compound X.(b) A molecular weight determination showed that compound X has a molecular weight of approximately 117. Find the molecular formula of compound X.(c) Many possible structures have this molecular formula. Draw complete structural formulas for four of themarrow_forward1. LDA, THF 2. CH3I, HMPA 3. H*, H2Oarrow_forwardPyrethrins, such as jasmolin II(below), are a group of naturalcompounds synthesized by flowers of the genus Chrysanthemum(known as pyrethrum flowers) to act as insecticides.(a) Circle and name the functional groups in jasmolin II.(b) What is the hybridization of the numbered carbons?(c) Which, if any, of the numbered carbons are chiral centers?arrow_forward
- Write the contributing resonance structures and resonance hybrid for each of the following: (a) CH;CH=CH-CH=OH (f) CH3 (b) CH2=CH-CH-CH=CH2 (g) CH3-S-CH, (h) CH3-NO, (d) CH2=CH-Br CH, (e)arrow_forwardThere are two C–C single bonds in penta-1,3-diyne. (a) Which of those bonds would you expect to be stronger? (b) Which of those bonds would you expect to be shorter? (c) The molecule is moderately polar, with a dipole moment of 1.37 D. In which direction would you expect the dipole moment to point? Explain. Penta-1,3-diynearrow_forward2.33 Classify the following alcohols as primary, secondary, or tertiary: он OH (b) (e (e) OH (a) OH Oarrow_forward
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