Concept explainers
(a)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is:
The dash-wedge structure shows one hydrogen atom, two carbon atoms on the indicated bond, and the methyl group in one plane. One hydrogen atom on each carbon atom is oriented away from the viewer with bromine, and one hydrogen atom is oriented towards the viewer. For the purpose of determining the positions of the groups in the Newman projection, the carbon bearing the bromine
Newman projection represents a molecular structure looking along a particular bond.
(b)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure shows two groups
Newman projection represents a molecular structure looking along a particular bond.
(c)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is:
It shows that the carbon on the indicated bond along with
Looking along the indicated bond in
Newman projection represents a molecular structure looking along a particular bond.
(d)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is:
The molecule is substituted cyclopentane. The two groups on each of the carbons C2 and C3 are in axial-equatorial positions. On C3, both are hydrogen atoms. On C2, one is a methyl group in the axial position, and the other is hydrogen in equatorial position.
Looking along the indicated bond in
Therefore, the Newman projection of the given molecule can be drawn as:
Newman projection represents a molecular structure looking along a particular bond.
(e)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is:
The molecule is substituted cyclopentane. The two groups attached to the ring carbon C2 are methyl in an equatorial up position and hydrogen in an axially down position. The two groups attached to C3 are both hydrogens, one in axial up position and the other in equatorial down position. Looking down the indicated bond in the
The Newman projection of the molecule can therefore be drawn as
Newman projection represents a molecular structure looking along a particular bond.
(f)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is:
The molecule is substituted cyclohexane in a chair conformation. The methyl groups on the two carbons (C2 and C3) on the indicated bond are both in equatorial positions. The other two groups, both hydrogens, are in axial positions. Looking along the indicated bond in the
Newman projection represents a molecular structure looking along a particular bond.
(g)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is
The molecule is substituted cyclohexane in a chair conformation. The two groups attached to C1 are bromine in axial down position and hydrogen in equatorial up position. The two groups attached to C2 are methyl in axial up position and hydrogen in equatorial down position. Looking down the indicated bond, the bromine on the front carbon (C1) and the methyl group on the back carbon (C2), in the Newman projection, will appear straight up and straight down respectively, in staggered positions. The hydrogen on front carbon C1 will appear going to the left, slanted up. The hydrogen on back carbon C2 will appear going left, slanted down. The rest of the ring will appear on right with C6 carbon, on the front. slanted up. C3 carbon, on the back, will appear going to right, slanted down.
The Newman projection of the molecule can then be drawn as
Newman projection represents a molecular structure looking along a particular bond.
(h)
Interpretation:
The Newman projection for the species shown is to be drawn looking down the bond indicated in red.
Concept introduction:
A Newman projection is used to visualize the conformation of a molecule by representing it as viewed down the bond of interest. The dot represents front atom, and the circle represents the back atom. The bonds to the front carbon converge on the central point while the bonds to the back carbon end on the circle.
Answer to Problem 4.26P
Newman projection of the given structure is:
Explanation of Solution
The dash-wedge structure of the molecule is
The molecule is substituted cyclohexane in boat conformation. The two groups on C1 are
Looking down the indicated bond, the
Newman projection represents a molecular structure looking along a particular bond.
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Chapter 4 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- Draw the Newman projection of the following compound looking down the bond indicated via the arrow. ( see picture)arrow_forwardDraw Newman projections of the following molecules viewed from the direction of the blue arrows.arrow_forwardDraw the potential energy of the molecule circled at the top. Draw the other 3 Newman projections based on the one already drawn by rotating the back carbon clockwise. Explain your answersarrow_forward
- You move along your journey in the Plane of the Page to encounter. pseudoephedrine (below), the principal ingredient the common cold medication Sudafed. Answer the following question about this molecule. Draw Newman Projections for the two indicated bonds.arrow_forwardWithout rotating the bond, draw a proper Newman structure of the following molecule, looking down the bond in the direction of the arrow. [Select] [Select] OH Br [Select] [ Select ]arrow_forwardDraw the two most stable forms of this molecule. Identify which is lowest and highest in energy with an explanation.arrow_forward
- For the same molecule, which of the images corresponds to the correct Newman projection along the indicated bond? Need help understaniding how to answer question?arrow_forward(a) Draw the Newman projection for each molecule shown here, looking down the C-C bond indicated by the arrow. (b) Which configuration do you think is more stable? Explain. H3C' *CH3 H3C 'CH3 cis-1,2-Dimethylcyclopropane trans-1,2-Dimethylcyclopropanearrow_forwardDescribe with words how you would draw the curved arrow(s) to get to the more stable resonance form for the left-hand pair. Be sure to include how many curved arrows are needed and what atom (or bond) the electrons are coming from or going to. Do the same for the resonance pair on the right-hand side. more stable more stablearrow_forward
- Draw the most stable Newman projection for the following alkanes looking down the C-C bond pointed to by the arrows.arrow_forwardFill in the Newman projection for the following molecule from the angle shownarrow_forwardObserve the Newman projection of the next molecule along the bond shown in red with the front carbon the one bonded to "Cl". a) Draw one of the Newman projections of the molecule with a staggered conformation. b) Draw one of the Newman projections of the molecule with an eclipsed conformation.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning