ORG CHEM LL W/ LL SG&CONPLUS PKG>IC<
5th Edition
ISBN: 9781260069228
Author: SMITH
Publisher: MCG CUSTOM
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Question
Chapter 4, Problem 4.57P
Interpretation Introduction
(a)
Interpretation: The orientation of
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(b)
Interpretation: The location of substituent on
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(c)
Interpretation: The orientation of an equatorial
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(d)
Interpretation: The orientation of substituent
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
Interpretation Introduction
(e)
Interpretation: The location of substituent on
Concept introduction: Cis–trans isomers are geometrical isomers. Cis-isomer contains two groups on the same side of the ring. Trans-isomer contains two groups on the opposite side of the ring.
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Answer the following questions about compound A, which contains a CH3 group and OH group bonded to the carbon skeleton that consists of three six-membered rings in the conformation shown.a.Are the CH3 and OH groups oriented cis or trans to each other?
b. Is a substituent on Ca that is cis to the CH3 group located in the axial
or equatorial position?
c. Is an equatorial Br at Cb oriented cis or trans to the OH group?
d. Is the H atom on Cc located cis or trans to the OH group?
e.Is a substituent on Cd that is trans to the OH group located in the axial or equatorial position?
Sight 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.
Draw the structure of each molecule below and put an asterisk on each tetrahedral stereocenter.
i) 3,4-dichlorohexane
ii) 3-bromo-1-iodo-5-methylhexane
iii) 3-bromo-2,4-dimethylpentane
Chapter 4 Solutions
ORG CHEM LL W/ LL SG&CONPLUS PKG>IC<
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...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 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Draw the bond-line formula of 3,4-dimethylhexane. Is geometric isomerism observed in 3,4-dimethylhexane? What structural features must be present for stereoisomers to exist? (4 marks) (b) (1) Using Fischer projection, draw all the stereoisomers of 3-chloro-2-hydroxypentanoic acid. (4 marks) (ii) Assign the chiral centre(s) with R/S configurations in part (b)(i). Indicate which are enantiomers, diastereomers and meso compounds (if any).arrow_forwardOn the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose in Chapter 25). (a) Convert the stereorepresentation on the left to a planar hexagon representation. (b) Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?arrow_forwardFollowing is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?arrow_forward
- Glucose is a simple sugar with five substituents bonded to a six-membered ring.a. Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.b. Convert this representation into one that uses a hexagon with wedges and dashed wedges.c. Draw a constitutional isomer of glucose.d. Draw a stereoisomer that has an axial OH group on one carbon.arrow_forwardUse a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2¬C3 bondarrow_forwardUsing the cyclohexane with the C's numbered as shown, draw a chair form that fits each description. a.) The ring has an axial CH3 group at C1 and an equatorial OH on C2.b.) The ring has an equatorial CH3 group on C6 and an axial OH group on C4.c.) The ring has equatorial OH groups on C1, C2, and C5.arrow_forward
- Using the cyclohexane with the C’s numbered as shown, draw a chair form that fits each description. a. The ring has an axial CH3 group at C1 and an equatorial OH on C2. b. The ring has an equatorial CH3 group on C6 and an axial OH group on C4. c. The ring has equatorial OH groups on C1, C2, and C5.arrow_forwardRank the following groups in order of decreasing priority. −C≡CH, −CH(CH3)2, −CH2CH3, −CH=CH2arrow_forwardIs the reaction of 2-butene with HBr regioselective? a. Is it stereoselective? b. Is it stereospecific?arrow_forward
- Draw the planar (Haworth) structure for cis-1-ethyl-2- methylcyclohexane. (b) Draw the two ring - flipped chair conformations. (c) Circle the more stable chair conformation (circle both if they are equal in energy). Draw the Haworth structure and the two ring-flipped conformations of 1, 2, 4- trimethylcyclohexane (Compound D) on the frames below, b) Circle the more stable chair conformation (circle both if they are equal in energy). Haworth Structurearrow_forward1. Use a Newman projection about the indicated bond to draw the most stable conformer for each compound. (a) 3-methylpentane about the C2 ¬ C3 bond (b) 3,3-dimethylhexane about the C3 ¬ C4 bond2. refer to the questions below:arrow_forwardConsider the tricyclic structure B. (a) Label each substituent on the rings as axial or equatorial. (b) Draw B using chair conformations for each six-membered ring. (c) Label the atoms on the ring fusions (the carbons that join each set of two rings together) as cis or trans to each other.arrow_forward
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