Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 4.12, Problem 21P
Classify the ring carbons as up
. 
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a) Draw all Newman projections
of your molecule's conformations
in which the CH3 group and the
H of the CHY2 group are
positioned 'ANTI' to each other.
Be sure to put in the correct X
and Y atoms, bonded to the
correct C atoms, for your
molecule. X = FY=I
Conformations = 60 deg and
-
180 deg 60 deg dihedral angle
= - 179.987 deg 180 deg ·
-
dihedral angle
=
179.814 deg
Select all of the asymmetric carbon atoms in the following structure. A selected atom will turn green.
но
Draw the ve constitutional isomers that have molecular formula C5H10 and contain one ring.
Chapter 4 Solutions
Organic Chemistry (6th Edition)
Ch. 4.1 - Prob. 1PCh. 4.1 - Problem 4.2 Which of the following is not another...Ch. 4.1 - Problem 4.3 Draw the five constitutional isomers...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.2 - Draw the five constitutional isomers that have...Ch. 4.4 - Problem 4.7 Give the IUPAC name for each...Ch. 4.4 - Give the IUPAC name for each compound. a....Ch. 4.4 - Problem 4.9 Give the structure corresponding to...Ch. 4.4 - Prob. 10P
Ch. 4.5 - Give the IUPAC name for each compound.Ch. 4.5 - Give the structure corresponding to each IUPAC...Ch. 4.8 - Arrange the following compounds in order of...Ch. 4.9 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4.9 - Prob. 15PCh. 4.9 - Prob. 16PCh. 4.10 - Problem 4.17 a. Draw the three staggered and...Ch. 4.10 - Problem 4.18 Rank the following conformations in...Ch. 4.10 - Problem 4.19 Consider rotation around the...Ch. 4.10 - Calculate the destabilization present in each...Ch. 4.12 - Problem 4.21 Classify the ring carbons as up or...Ch. 4.12 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4.13 - Draw a second chair conformation for each...Ch. 4.13 - Problem 4.24 Draw both conformations for and...Ch. 4.13 - Problem 4.25 Draw the structure for each compound...Ch. 4.13 - Prob. 26PCh. 4.14 - Prob. 31PCh. 4.14 - Prob. 32PCh. 4.15 - Prob. 33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 42PCh. 4 - 4.46 Considering rotation around the bond...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 66PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 74PCh. 4 - Prob. 75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- Using your model of butane (CH3CH2CH2CH3) , complete the following graph of the anglebetween the two Me groups vs. potential energy. a. Label each Newman projection of butane on the graph with the words staggered, eclipsed, gauche, and anti, as appropriate. (Note that some structures will have more than one label.) b. Draw a wedge and dash bond representation of butane in its lowest P.E. conformation.arrow_forwardSight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forwardProvide the correct IUPAC name for the skeletal (line-bond) structure shown here. 2- 3- 2,2- 6- 6,6- || 3,3- tert- tri di tetra iso eth oct non meth pent hept ene yne ane ylarrow_forward
- Provide the correct IUPAC name for the skeletal (line-bond) structure shown here. 2- 2,2,2,2- 2,3-|| 2,2- 3- 3,3- tetra tri di hex eth but meth hept pent yne ane ene ylarrow_forwardDraw the skeletal (line-bond) structure of [C6H5SO3]-. Include all lone pairs and charges as appropriate.arrow_forwardWhich of the following is the highest energy chair conformer of the most stable isomer of 1-ethyl-2,4-dimethylcyclohexane? A | B II C) III IV = || ||| > INarrow_forward
- Tag each carbon atom in the main chain of the molecule drawn below. H | HIC-H H H 1 I H-C-C-C | | | H H H H | -C H H 11 H-C-C-H -C-H | H H | - - HI H-C-C-C-H H H H-C-H 1 H | Harrow_forwardWhat are these 2?arrow_forwardFollowing is the Structural formal of Chloropropane H H H 2. H Draw Newman projections for all staggered and eclipsed conformation formed by rotation about C1 - C2 bond from 0° to 360°. b) Which Staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy, which has thhe highest energy?arrow_forward
- 7. Draw curved arrows indicating the movements of electrons between the following pair of resonance structures. Name the pattern of resonance shown. What is the hybridization of the carbon atoms? 8. Draw the remaining three resonance structures for the molecule in problem 7 above. 9. There are several possible forms of a trisubstituted cyclohexane with the formula C10H200. I have drawn four of them. From these, which one do you think is most commonly naturally occurring, and why? Which is least commonly occurring and why? HO HO" HO HOarrow_forwardWrite the condensed and skeletal structures of the given molecule.arrow_forwardShow the delocalization of charges in the following structures. Draw the resonance forms and indicate the movement of electrons with curved arrows. Hint: First draw the Lewis structure for each the compound CH₂-CH=CH-OH e CH₂-CH=CH-CNarrow_forward
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