ORGANIC CHEMISTRY-MOLYMOD PACKAGE
5th Edition
ISBN: 9781260227307
Author: SMITH
Publisher: MCG
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Chapter 4, Problem 4.26P
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2,3-Dibromoprop-1-ene (C3H4Br2) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to
yield a molecule with the formula C3H3Br,Cl. (a) Identify two H atoms where this substitution would yield constitutional
isomers of C3H3Br,CI; (b) enantiomers of C3H3Br,Cl; (c) diastereomers of C3H3Br,Cl.
H
нн
H
Br
Br
2,3-Dibromoprop-1-ene
For each of the compounds below, state its systematic
name, its functional group(s), and whether or not it is chi-
ral.
CH3 O
С—ОН
CH-CНCHC—О
NH
(a)
Ć (b)
CH-CH-CH3CHСНЗ
CH;CH,CH3
(c)
(d)
Butanal (C4H&O) has eight H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule
with the formula C4H¬CIO. (a) Identify two H atoms where this substitution would yield constitutional isomers of C4H7CIO;
(b) enantiomers of C4H;CIO; (c) conformers of C4H;CIO.
H.
H
H
H
нн
H
Butanal
O=U
Chapter 4 Solutions
ORGANIC CHEMISTRY-MOLYMOD PACKAGE
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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- Name or write the condensed structural formula for the fol- lowing compounds: (a) trans-2-pentene (b) 2,5-dimethyl-4-octene (c) CH3 CH;CHCH,CH3 C=C `H. CH;CH2, H СООН H CH3 CH CH3 CH3 `CH2 (d)arrow_forwardName or write the condensed structural formula for the fol- lowing compounds: (a) trans-2-pentene (b) 2,5-dimethyl-4-0octene (c) CH3 CH;CH2 CH,ĊHCH,CH3 Н `H (d) Br Br (e) CH-CHЗ НС—ССH-CСНЗ ČH3arrow_forwardDraw structural formulas of the following in a condensed formarrow_forward
- Which of the following alkenes can exist as cis-trans isomers? Write their structures. (a) CH2=CHCH2CH3 (c) CH2=C(CH3)2 (b) CH3CH=CHCH3 (d) CH3CH2CH=CHCIarrow_forwardDraw the skeletal structures of the following molecules.(a) (4E)-2,4-dimethyl-1,4-hexadiene (b) cis-3,3-dimethyl-4-propyl-1,5-octadiene (c) trans-2,2,5,5-tetramethyl-3-hexenearrow_forward(b) NABH, CH3 COCH,CH3 CH3CH2OH (c)arrow_forward
- Draw the structure of (a) 4-isopropylheptane (b) 1,1-dichlorocyclopentane (c) cis-3-octenearrow_forwardDraw the structures for the following compounds.(a) 3-benzyl-4-bromohexane , 4,4-dimethylcyclohexene(b) trans-4,5-dibromohex-2-ene , cis-1,1-dibromo-2-ethyl-2,3-dimethylcyclobutanearrow_forwardEach of the following names is wrong. Draw structuresbased on them, and correct the names:(a) 3,3-dimethylbutane(b) 1,1,1-trimethylheptane(c) 1,4-diethylcyclopentane(d) 1-propylcyclohexanearrow_forward
- Each of the following names is wrong. Draw structuresbased on them, and correct the names:(a) 3,3-dimethylbutane (b) 1,1,1-trimethylheptane(c) 1,4-diethylcyclopentane (d) 1-propylcyclohexanearrow_forwardDraw the skeletal (bond-line) structures of all isomers of C4H8O (including configurational isomers) that contain an alkene and an ether. There should be 5 structures.arrow_forwardDraw structures from the following names, and determine which compounds are optically active:(a) 1,3-dichloropentane (b) 3-chloro-2,2,5-trimethylhexane(c) 1-bromo-1-chlorobutanearrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License