Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 4.SE, Problem 59AP
Interpretation Introduction
Interpretation:
The three- dimentional representation of amantadine, showing the chair cyclohexane rings are to be drawn.
Concept introduction:
Tricyclic compounds like amantadine four bridgehead carbons. Each ring can be in the chair conformation.
To draw:
The three- dimentional representation of amantadine, showing the chair cyclohexane rings.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
A is a toxin produced by the poisonous seaweed Chlorodesmis fastigiata. (a) Label each alkene that exhibits stereoisomerism as E or Z. (b) Draw a stereoisomer of A that has all Z double bonds.
Draw all stereoisomers formed when each alkene is treated with CHCl3 and KOC(CH3)3.
Draw the products formed when each alkene is treated with BH3 followed by H2O2,HO−. Include the stereochemistry at all stereogenic centers.
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- (a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?arrow_forwardDraw the product obtained when cis-2-butene is treated first with Br2 in CH2Cl2, second with NaNH2 in NH3, and then finally with Li in NH3.arrow_forwardWhat is the major stereoisomer formed when attached alkyl halide is treatedwith KOC(CH3)3?arrow_forward
- Draw the products formed when both cis- and trans-but-2-ene are treated with a peroxyacid followed by -OH (in H2O).Explain how these reactions illustrate that anti dihydroxylation is stereospecic.arrow_forwardConvert the following Fischer projections into tetrahedral representations, and assign R or S stereochemistry to the molecules on part a and b in the picturearrow_forward(a) Which double bonds in (E)-ocimene, a major component of the odor of lilac owers, can exhibit stereoisomerism? (b) Draw a diastereomer of (E)-ocimene.arrow_forward
- Rank the following groups in order of decreasing priority. a. – COOH, – H, – NH2, – OH b. – H, – CH3, – Cl, – CH2CI c. -CH2CH3, -CH3, -H, -CH(CH3)2 d. – CH = CH2, – CH3, – C ≡ CH, – Harrow_forwardBogorol A is a natural product with the potential to fight antibiotic-resistant bacteria. Shown below is an intermediate that was used in a synthesis of bogorol A. Assign the configuration of the alkene unit as either Z or E. a. Z b. Earrow_forwardDraw the products formed when attached alkene is treated with BH3 followed by H2O2, HO−. Include the stereochemistry at all stereogenic centersarrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you