(a)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
Hybridization: hybridization is mixing of valence atomic orbitals to get equivalent (equally energetic) hybridized orbitals. Sp3 hybridized orbital has four orbitals. Sp3 hybridized carbon atom in a compound has 4 sigma bonds.
Identify: the sp3 hybridized carbon atoms in the cyclopentadiene.
(b)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
Most acidic proton of a compound depends upon the stability of conjugate base formed after the deprotonation.
Identify: most acidic proton presented in cyclopentadiene.
(c)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
Resonance structures: Resonance structures are electrically equivalent Lewis structures. Formal charges on these structures are same, these structures represented through a double headed arrow between the structures. Resonance structures are resulted during the delocalization of pi-bonding electrons and lone pair of electrons in the molecule.
To draw: resonance structures of cyclopentadienyl anion.
(d)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
Hybridization: hybridization is mixing of valence atomic orbitals to get equivalent (equally energetic) hybridized orbitals. Geometry can be predicted according to the hybridization of the molecule.
To find: the number sp3- hybridized carbon atoms present in cyclopentadienyl anion.
(e)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
Geometry is predicted according to the hybridization of the molecule. Hybridization: hybridization is mixing of valence atomic orbitals to get equivalent (equally energetic) hybridized orbitals.
To find: geometry of cyclopentadienyl anion.
(f)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
In bond-line structure, bonds between other than hydrogen atoms and lone pairs presented are shown. Number of hydrogen atoms attached to a carbon atom depends upon the number of other than hydrogen atoms bonded and lone pairs presented to that carbon atom. Covalence of carbon is four. So hydrogen atoms are presented accordingly if the counting of carbon atom’s bonds with other than hydrogen atom and lone pair of electrons are less than four.
To find: number of hydrogen atoms presented in the cyclopentadienyl anion.
(g)
Interpretation:
sp3 hybridized carbon atoms, most acidic proton, sp3 hybridized carbon atoms of conjugate base, geometry of conjugate base, number of hydrogen atoms in the conjugate base, number of lone pairs in the conjugate base and the resonance structure of conjugate base of cyclopentadiene are needed to find out.
Concept introduction:
Lone pairs of the molecules are electron pairs which do not participate in the sigma bonding of the molecule. It can participate in the delocalization of molecule.
To find: the lone pairs present in the cyclopentadienyl anion.

Want to see the full answer?
Check out a sample textbook solution
Chapter 3 Solutions
ORGANIC CHEMISTRY,SOLNS...-ETEXT+BOX
- Fina x | Sign X Sign X lab: X Intro X Cop) X a chat x My x Grad xLaur x Laur x a sheg X S Shoj XS SHE X acmillanlearning.com/ihub/assessment/f188d950-dd73-11e0-9572-0800200c9a66/d591b3f2-d5f7-4983-843c-0d00c1c0340b/f2b47861-07c4-4d1b-a1ee-e7db27d6b4ee?actualCourseld=d591b3f2- 5 © Macmillan Learning Organic Chemistry Maxwell presented by Macmillan Learning For the dehydrohalogenation (E2) reaction shown, draw the Zaitsev product, showing the stereochemistry clearly. H H KOH Br EtOH Heat Select Draw Templates More Erase // C H Q Search hp Q2 Q Δ קו Resouarrow_forwardIs the structural form shown possible given the pKa constraints of the side chains?arrow_forwardon x Fina X Sign X Sign x lab X Intro X Cop X chat X My x Grac x Laur x Laur x ashes x S Shox S SHE x a eve.macmillanlearning.com/ihub/assessment/f188d950-dd73-11e0-9572-0800200c9a66/d591b3f2-d5f7-4983-843c-0d00c1c0340b/f2b47861-07c4-4d1b-a1ee-e7db27d6b4ee?actualCourseld=d591b3f2-c stions estion. ct each urces. +95 Macmillan Learning Draw the product formed by the reaction of potassium t-butoxide with (15,25)-1-bromo-2-methyl-1-phenylbutane (shown). Clearly show the stereochemistry of the product. H BH (CH3)3CO-K+ +100 H3CW (CH3)3COH +85 H3CH2C +95 ossible ↓ Q Search Select Draw Templates More C H 0 bp A Erase 2Q 112 Resouarrow_forward
- Identify the structure of the PTH derivative generated after two rounds of Edman degradation.arrow_forwardUse the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 31 0.5 30 26 29 22 28 100 27 33 26 23 15 4 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. 妊 n ? Previous Nextarrow_forwardfor this question. Write the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M+ = 98.1106. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 1.008 12C 98.90 12.000 14N 99.63 14.003 160 99.76 15.995 Molecular formula (In the order CHNO, with no subscripts)arrow_forward
- PLEASE READ!!! I DONT WANT EXAMPLES, I DONT WANT WORDS OR PARAGRAPHS!!! PLEASE I UNDERSTAND THE BASICS BUT THIS IS AN EXCEPTION THAT EVEN THE INTERNET CANT HELP!!!! THIS IS THE THIRD TIME I'VE SENT THOSE QUESTIONS SO PLEASE DONT RESEND THE SAME STUFF, ITS NOT HELPING ME!!! I ALSO ALREADY TRIED TO DRAW THE MECHANISM MYSELF, SO IF ITS RIGHT PLEASE TELL ME OR TELL ME WHAT I HAVE TO CHANGE!!! First image: I have to SHOW (DRAWING) the mechanism (with arows and structures of molecules) NOT WORDS PLEASE! of the reaction at the bottom. Also I have to show by mecanism why the reaction wouldn't work if the alcohol was primary Second image: I have to show the mechanism (IMAGE) (with arrows and structures of the molecules) NOT WORDS PLEASE !! for the reaction on the left, where the alcohol A is added fast in one portion HOMEWORK, NOT EXAM!! ALL DETAILS ARE IN THE IMAGES PLEASE LOOK AT THE IMAGES, DONT LOOK AT THE AI GENERATED TEXT!!!arrow_forwardWrite the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M+ = 85.0899. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 1.008 12C 98.90 12.000 14N 99.63 14.003 160 99.76 15.995 Molecular formula (In the order CHNO, with no subscripts)arrow_forwardUse the data below from an electron impact mass spectrum of a pure compound to deduce its structure. Draw your structure in the drawing window. Data selected from the NIST WebBook, https://webbook.nist.gov/chemistry/ m/z Relative intensity 59 3.0 58 64 43 100 15 23 • You do not have to consider stereochemistry. •You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. + n[] 85 // ? CH4 Previous Nextarrow_forward
- Write the molecular formula for a compound with the possible elements C, H, N and O that exhibits a molecular ion at M* = 128.0632. Exact Masses of the Most Abundant Isotope of Selected Elements Isotope Natural abundance (%) Exact mass 1H 99.985 12C 98.90 14N 99.63 160 99.76 Molecular formula 1.008 12.000 14.003 15.995 (In the order CHNO, with no subscripts)arrow_forwardCan I please get help with this? And can I please the lowest possible significant number?arrow_forwardWhat is the molar mass of a gas that takes three times longer to effuse than helium?arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





