Concept explainers
(a)
Interpretation: The name of the given structure needs to be determined.
Concept Introduction: Chair conformation is the most stable conformation of cyclohexane. It is represented as follows:
Here, the substituted groups in the chair conformation are represented as follows:
The groups showing in straight upward and downward directions are axial and the groups bend slightly right or left are equatorial.
The axial and equatorial groups are represented in the chair conformation as A and E:
(b)
Interpretation: The given structure on the right needs to be completed which is obtained by chair flip.
Concept Introduction:After a chair flip, all the axial bonds become equatorial and all the equatorial bonds become axial. But, the groups in the up direction remains upward and groups in down direction remain downward.
Also, if the molecule is cis, it remains cis even after chair flip. The same is the case with trans molecule.
(c)
Interpretation: The name of the structure formed after the chair flip in part (b) needs to be determined.
Concept Introduction: Chair conformation is the most stable conformation of cyclohexane. It is represented as follows:
Here, the substituted groups in the chair conformation are represented as follows:
The groups showing in straight upward and downward directions are axial and the groups bend slightly right or left are equatorial.
The axial and equatorial groups are represented in the chair conformation as A and E:
(d)
Interpretation: Whether the two structures are consistent with the given facts about chair flip or not needs to be determined.
Concept Introduction:
The chair conformation of cyclohexane is represented as follows:
During the flipping, no bond is break. The numbering in the chair form is represented as follows:
During ring flipping, mirror image of the chair conformation is formed.
It is represented as follows:
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Chapter 7 Solutions
Organic Chemistry: A Guided Inquiry
- 1. Draw ethylbenzene and put a + on the carbon next to the benzene (innermost carbon in ethyl group). Show all resonance forms for this ion. 2. draw the naphthalene and put one - on the neighboring carbon of the "crossroads". show every resonance forms for this ion. 3. Draw benzoic acid and draw on all p-orbitals.arrow_forwardA student suggests that the molecule on the right can be made from a single molecule with one less ring in it. If the student is correct, draw the starting material below, otherwise, check the box under the drawing area. ? + NaOH Click and drag to start drawing a structure. olo Ararrow_forwardA. Draw the major resonance structure, then draw curved arrows to show how this can be converted to the Lewis structure given. B. Thionitromethane is redrawn for you. Draw curved arrows to show how this can be converted to the resonance structure you drew in part A.arrow_forward
- Glucose is a simple sugar with five substituents bonded to a six-membered ring.a. Using a chair representation, draw the most stable arrangement of these substituents on the six-membered ring.b. Convert this representation into one that uses a hexagon with wedges and dashed wedges.c. Draw a constitutional isomer of glucose.d. Draw a stereoisomer that has an axial OH group on one carbon.arrow_forwardShown below is Streptomycin, and Neomycin B. Circle and label as many functional groups in these molecules as you can. a. Label each chiral carbon in Streptomycin. How many total stereoisomers exist for Streptomycin? b. Label each chiral carbon in Neomycin B. How many total stereoisomers exist for Neomycin B?arrow_forwardConsider an oxygen atom contained in a neutral molecule, like those in Model 1. Give the name for the electrons around the oxygen that are not involved in a covalent bond. What bond angle is formed when oxygen forms two single bonds? What shape is formed? Which functional groups in Model 1 are polar? When a carbon atom forms a double bond to an oxygen atom, it is called a carbonyl group. Which functional groups in Model 1 contain a carbonyl group?arrow_forward
- Must answer completearrow_forwardConstruct a model in which a tetrahedral carbon atom has four different colored model atoms attached to it- red, green, orange and white representing 4 different atoms attached to the central atom. a) Does the atom have a plane of symmetry? why or why not? b) Now replace the green atom in your model with a second orange atom. Now two of the groups attached to the carbon atom are identical. Does the model now have a plane of symmetry? Describe it. c)A carbon atom has four different groups attached to the stereogenic center. Draw structural formulas for the following compound and mark stereogenic centers with as asterisk: 1-bromobutane, 2-bromobutane, 1,2-dibromobutane, 1,4-dibromobutane, 2,3-dibromobutane.arrow_forwardchair structures in organic chem. thank youarrow_forward
- QUESTION 2 Label the stereocenters (C and CA) as R or S, and then choose the correct name for Molecule W. (Note: R and S designations are placed in front of the name in parentheses. The number in front of the R or S indicates where the stereocenter appears in the base chain.) CI C2- Molecule W O A. (2R,4R)-2-chloro-4-fluorohexane O B. (2R,4S)-2-chloro-4-fluorohexane O C. (2S,4R)-2-chloro-4-fluorohexane O D. (2S,4S)-2-chloro-4-fluorohexanearrow_forwardComplete the mechanism of the given enamine to imine tautomerization by adding any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Then, indicate which of the species will predominate at equilibrium. NH-R is a generic acid with conjugate base :NH,-R in solution. Note the resonance arrows in the scheme. Step 1: add curved arrows. Step 2: complete the structure and add curved arrows. Select Draw Rings Groups More Erase Select Draw Rings Groups More Erase C H N /|の +) H,N -R H,N - R 1L H H. H H Harrow_forwardPlease helparrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning