Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 4, Problem 9PP
Interpretation Introduction
Interpretation:
The names for the mentioned bicyclic
Concept introduction:
For naming bicyclo-compounds:
Compounds containing two fixed or bridged rings are known as bicycloalkanes.
Then, the number of carbon atoms in each bridge is written in square brackets in decreasing order.
For numbering the substituent groups, start numbering from the longest chain to the middle-numbered chain and at last, the shortest chain.
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The skeletal line formula for a branched alkene is shown below. (i) What is the molecular formula of this compound? (ii) How many carbon atoms are in the longest chain, ignoring the double bond? (iii) What is the longest chain incorporating both carbons of the double bond? (iv) How many substituents are on this chain? (v) Give the IUPAC name for this compound. [6]
2.46 Give IUPAC names for the following alkanes:
(а)
CH3
(b)
CH3
CH3CHCH2CH2CHЗ
CH3CH2CCH3
CH3
(c) H3C CH3
(d)
CH2CH3
CH3
CH3CHCCH2CH2CH3
CH3CH2CHCH,CH2CHCH3
CH3
(e)
CH3 CH2CH3
(f) H3C CH3
CH3CH2CH2CHCH2CCH3
CH3C-CCH2CH2CH3
CH3
H3C CH3
1. Write condensed structural formula for all isomers of compounds that fulfill the following
requirements:
(a) Alkenes with molecular formula CsH10.
(b) Alkynes with molecular formula C4H6.
(c) Dienes with molecular formula C4H6.
2. For each of the following, give the order of increasing boiling point:
(a) n-Heptane, n-octane and n-hexane.
(b) n-Pentane, isopentane and n-hexane.
(c) 2-Methylhexane, n-heptane and 3,3-dimethylpentane.
9
3. Isomeric compounds can sometimes be distinguished by observing the number of mono-
brominated compounds that each forms. In the following cases decide which isomer is
present by the number of compounds that are formed.
(a) Compound A forms four monobromo compounds. Is it 2-methylbutane or n-pentane?
(b) CompoundB forms four monobromo compounds. Is it 2- methylpentane or 3-
methylpentane?
(c) Compounds C
forms
monobromo compound. Is it cyclopentane or
one
mehtylcyclopentane?
4. A hydrocarbon C5H12 was allowed to react with bromine. Only monobromo…
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
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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
- Write structural formulas for all the constitutionally isomeric compounds having the given molecular formula.(a) C4H10(b) C5H12(c) C2H4Cl2(d) C4H9Br(e) C3H9Narrow_forwardWhich of the following is true about the carbon-carbon single bond in 1,3-butadiene when compared to the carbon-carbon single bond in ethane? (A) It is shorter than the carbon-carbon single bond of ethane. (B) The single bond in 1,3-butadiene has a higher %s character than in ethane The hydrogen atoms push the carbons closer using electrocyclic forces. Both A and B. (E) None of the above.arrow_forwardon 2.39 Using the method outlined in Section 2.17, give an IUPAC name for each of the following alkyl groups, and classify each one as primary. secondary, or tertiary: (a) CH₂(CH₂CH₂- (b)-CH,CH,CHCH,CH,CH, CH,CH, (c)-C(CH₂CH₂) (d) -CHCH,CH,CH, (0) B) -CH₂CH₂- CH- CH₂arrow_forward
- Write structural formulas for compounds that meet the following descriptions:(a) A 6-carbon alkene whose longest chain is 4 carbons inlength (three possibilities)(b) An alkyne with 5 carbons total (three possibilities)(c) A monosubstituted benzene with a total of 8 carbons(one possibility)(d) A disubstituted benzene with a total of 8 carbons(three possibilities)arrow_forward5.76 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 C3H3Br₂Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br₂Cl; (b) enantiomers of C3H3Br₂Cl; (c) diastereomers of C3H3Br₂Cl. co 11 HHH Juods H Brugtrio 2 bas A 2,3-Dil so ontemme A chon Br 2,3-Dibromoprop-1-enearrow_forward2.34 Consider 1-bromopropane, CH3CH2CH2Br.(a) Draw a Newman projection for the conformation in which !CH3 and !Br are anti (dihedral angle 1808).(b) Draw Newman projections for the conformations in which !CH3 and !Br are gauche (dihedral angles 608 and 3008).(c) Which of these is the lowest energy conformation?(d) Which of these conformations, if any, are related by reflection?arrow_forward
- Write the systematic names of the following alkanes. (a) CH3CH2CH2CH2CH3(b) CH3−CH3(c) CH3−CH2–CH2−CH3(d) CH3−CH2–CH2−CH2–CH2−CH2–CH2−CH3(e) CH4(f) CH3CH2CH3arrow_forward4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4- Dibromocyclohexane. 4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-Dibromocyclohexane. 4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4- Dibromolcyclohexane. Explain the reason for your choice.arrow_forward3B. For each compound below, draw two chair conformations. Indicate whether the substituents are axial or equatorial. Indicate which chair conformation is more stable. (you need to draw conformations of the exact molecule, not its mirror image or diastereomer) (a) (b) (c) Ме Me Et "Et Et Mearrow_forward
- For each of the following compounds, identify all groups that would be considered substituents and then indicate the systematic name for each compound. (a) (b) (d) (e)arrow_forwardIf either of the following molecules has a stereogenic carbon (chirality center), give structures for both of the enantiomers. (a) 2-bromopropane (b) 2-bromobutanearrow_forwardFor each of the following molecular formulas, determine the number of elements of unsaturation,and draw three examples.(a) C4H4Cl2 (b) C4H8Oarrow_forward
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