Interpretation:
The structure for all the compounds with the molecular formula
Concept introduction:
Infrared spectroscopy is a simple, instrumental technique, which helps to determine the presence of various
It depends on the interactions of atoms or molecules with the
The molecules that have dipole moment are IR active and the molecules that do not have dipole moment are IR inactive.
The carbon–carbon double bond
The carbon–carbon triple bond
The alcohol or phenol
The ether
Degree of unsaturation is the calculation that determines the total number of rings and pi-bonds.
It is used in organic chemistry to draw chemical structures.
Mathematically, the degree of unsaturation is expressed as
Here,
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Chapter 2 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- In Section 15.5c, we learned that the frequency of the C=0 stretch for an amide is lower than it is for a ketone, suggesting that the C=0 bond is weaker in an amide. This weakening of the C=0 bond can be explained by the significant contribution from one of its resonance structures toward the resonance hybrid. Draw that resonance structure for N,N-dimethylacetamide [CH3CON(CH3)2] and explain how it accounts for the weakening of the C=0 bond.arrow_forwardThe naphthalene molecule has a structure that corre- sponds to two benzene molecules fused together: The ™ electrons in this molecule are delocalized over the entire molecule. The wavelength of maximum absorption in benzene is 255 nm. Will the corresponding wavelength in naphthalene be shorter or longer than 255 nm?arrow_forward9) Deduce the structure of an unknown compound with molecular formula C5H80 using information given by its infrared spectrum Frequency (cm-1): 3100, 2950, 2800, 1695, 1610,1450, 1375 HOarrow_forward
- For each organic compound in the table below, enter the locant of the highlighted side chain. CH3 CH,— CH,— CH— CH, CH3 1 compound CH₂ | CH,—C− CH,—CH — CH CH3 モー CH3 CH,—CH— CH,—C— CH | CH₂ CH3 CH3 | CH3 locant of highlighted side chain 0 X Sarrow_forward(a) Describe the molecular geometry expected for 1,2,3-butatriene (H2C=C=C=CH2). (b) Two stereoisomers are expected for 2,3,4-hexatriene (CH3CH=C=C=CHCH3). What should be the relationship between these two stereoisomers?arrow_forwardConsider a molecule with the molecular formula of C3H7NO2. The IR and ¹H NMR spectra are shown below. Draw the structure that best fits this data. 4000 3000 2H 2000 1500 Wavenumbers (cm-¹) + 2H 1000 3H 500 ppmarrow_forward
- The NMR spectrum of bromocyclohexane indicates a low field signal (1H) at δ 4.16. To room temperature, this signal is a singlet, but at -75 ° C it separates into two peaks of unequal area (but totaling one proton): δ 3.97 and δ 4.64, in ratio 4.6: 1.0. How do you explain the doubling in two peaks? According to the generalization of the previous problem, what conformation of the molecule predominates (at -75 ° C)? What percentage of the molecules does it correspond to? Solve all parts otherwise down vote and hand written solutionarrow_forwardDraw the structures of the four primary (1°) amines with molecular formula C5H13N that contain a chain with 4 carbon atoms in the longest continuous carbon chain. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.arrow_forwardView and analyze the given spectroscopic data of an unknown compound with molecular formula C8H10O Propose a structure based on your analysis. Support your answer by interpreting the given spectroscopic data.arrow_forward
- Draw the structure of the two tertiary (3°) amines with molecular formula C6H15N that contain a group with 3 carbon atoms in the largest group. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.arrow_forwardA C¬D (carbon–deuterium) bond is electronically much like a C¬H bond, and it has a similar stiffness, measured by the spring constant, k. The deuterium atom has twice the mass (m) of a hydrogen atom, however. A chemist dissolves a sample in deuterochloroform (CDCl3) and then decides to take the IR spectrum and simply evaporates most of the CDCl3. What functional group will appear to be present in this IR spectrum as a result of theCDCl3 impurity?arrow_forwardSuppose you have two bottles, labeled ketone A and ketone B. You know that one bottle contains CH3CO(CH2)5CH3 and one contains CH3CH2CO(CH2)4CH3, but you do not know which ketone is in which bottle. Ketone A gives a fragment at m/z = 99 and ketone B gives a fragment at m/z = 113. What are the likely structures of ketones A and B from these fragmentation data?arrow_forward
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