Concept explainers
Interpretation:
Cumulene has three adjacent double bonds. An orbital picture of cumulene is to be drawn. The state of hybridization of the two central carbons is to be given. The geometric relationship of the substituents on one end to those at other end is to be given. The isomerism possible is to be stated.
Concept introduction:
A sp2 hybridized carbon can form three σ bonds and one π bond. A sp hybridized carbon can form two σ bonds and two π bonds. The model of cumulene constructed shows the molecule is planar. A planar molecule with double bond can exhibit geometrical isomerism.
To draw:
The orbital picture of cumulene.
To give:
The state of hybridization of the two central carbons and the geometric relationship of the substituents on one end to those at other end.
To state:
The isomerism possible in cumulene.
Want to see the full answer?
Check out a sample textbook solutionChapter 9 Solutions
Organic Chemistry
- What is a hydrocarbon? What is the difference between a saturated hydrocarbon and an unsaturated hydrocarbon? Distinguish between normal and branched hydrocarbons. What is an alkane? What is a cyclic alkane? What are the two general formulas for alkanes? What is the hybridization of carbon atoms in alkanes? What are the bond angles in alkanes? Why are cyclopropane and cyclobutane so reactive? The normal (unbranched) hydrocarbons are often referred to as straight-chain hydrocarbons. What does this name refer to? Does it mean that the carbon atoms in a straight-chain hydrocarbon really have a linear arrangement? Explain. In the shorthand notation for cyclic alkanes, the hydrogens are usually omitted. How do you determine the number of hydrogens bonded to each carbon in a ring structure?arrow_forwarda. How many Lewis structures have the formula C4H11N? 10 b. In how many of the structures is the nitrogen atom attached to only one carbon? c. How many of them have carbon-carbon double bonds? d. How many of them have carbon-nitrogen double bonds? e. How many of them have rings? f. How many of the structures are capable of hydrogen bonding? g. How many of the structures contain a carbon atom attached to three other carbons? h. How many of the structures contain a nitrogen atom attached to three carbons? Varrow_forward3. Draw the structure of the following alkenes. Some of these compounds can show isomerism, and some cannot. Indicate which among these can show cis and trans isomers. a. hex-3-ene b. buta-1,3-diene c. 2,3-dimethylpent-2-ene 4. Draw the structure of the following alkenes. Some of these compounds can show isomerism, and some cannot. Indicate which among these can show cis and trans isomers. a. 3-ethylhexa-2,4-diene b. pent-1,3-diene c. 3,7-dichloroocta-2,5-dienearrow_forward
- Find the incorrect statement about alkynes. * A- Alkynes do not show isomerism. B- The triple bond of an alkyne is shorter than the single bond in an alkane. C- A pi-bond in an alkyne is formed by sideways overlap of p orbitals standing perpendicular on sp hybridised carbon atoms. D- All of these statements are correct. E- None of these statements are correct.arrow_forwarda. C4H8 + Cl2 -----> C4H8Cl2 b. C6H6 + Cl2 -----> C6H5Cl + HCl c. C3H6 + HCl -----> C3H7Cl Do they have an addition reaction? please explainarrow_forward6. Briefly identify the important differences between an alkene and an alkyne. How are they similar? A. The alkene (CH3)2CHCH2CH=CH2 is named 4-methyl-1-pentene. What is the name of (CH3)2CHCH₂C=CH? B. Do alkynes show cis-trans isomerism? Explain.arrow_forward
- 2. Draw the mechanism of the bromination of acetylene: 3. Draw the structures of the following: a. 3-bromo-3,4-dimethyl-1-hepten-5-yne b. Acetylene c. 1-ethynyl-2-methylcyclohexanearrow_forward1. Which of the following compounds are isomers of each other? I. 3-hexene II. Cyclohexane III. 2,3-dimethyl-2-butene IV. 2-methyl-2,3-pentadiene a. I and II b. II and IV c. I, II, III d. I, II, III, IV 2. Which of the following does not contain a carbonyl group? A. CH3CH2CH2COCH2CH3 B. CH3CH2CH2COOCH3 C. CH3CH2CH2CHOHCH2CH3 D. CH3CH2CH2CONH2CH3arrow_forwardHow does the structure of an alcohol differ from an ether? Describe how an aldehyde differs in structure from a ketone. Thiols are compounds which resemble alcohols, except that the oxygen atom is replaced by a sulfur atom. Draw the analogous thiol for the four carbon alcohol in Table 1. Describe the structural difference between carboxylic acids and esters. Are ethers polar molecules? Would you expect ethers to have higher or lower boiling points than alkanes (circle one)? Explain. Pentane (an alkane) has a boiling point of 36 °C. Does the data agree with your prediction? explain why this could be the casearrow_forward
- Pyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. CH3 CH2=CH-CH. CH-C- -HCS 0-CH, CH,-C H2C- ČH, Which is not a functional group or structural feature in jasmolin II? cycloalkane carboxylic acid ester alkenearrow_forwardPart II - Isomerism 1. Octane, C8H18, has 18 different constitutional or chain isomers. One of them, isooctane, is used as a standard in determining the octane rating of gasoline a. Draw the structural formulas for at least ten chain isomers of octane. b. Give the IUPAC name of each. c. Which of the isomers that you have drawn has the highest boiling point? Which has the lowest boiling point? Rationalize.arrow_forwardPart II - Isomerism 1. Octane, C8H18, has 18 different constitutional or chain isomers. One of them, isooctane, is used as a standard in determining the octane rating of gasoline a. Draw the structural formulas for at least ten chain isomers of octane. b. Give the IUPAC name of each. c. Which of the isomers that you have drawn has the highest boiling point? Which has the lowest boiling point? Rationalize. 2. Which of the following structural formulas represent identical compounds and which represent constitutional/structural isomers? Identical compounds: Constitutional isomers: CH3 i). CH3-C-CI ČH3 a). CH3CH2CHCH3 e). CH2CH2CHCH3 CI CI CI CH,CI b). CH3-C-CH3 f). CH3CH2CH2CH,CI j). CICH2 CI CH3 g). CICH,CHCH3 CH2CI k). CH3-CH-CH3 CI c). CH3CHCHCH3 CH2CH3 1). CH3CHCI h). CH3CHCH2CH2CI CI d). -CIarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
- Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning