Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 4, Problem 51P
Interpretation Introduction
Interpretation:The structure of cyclodecane in a chair conformation needs to be compared with trans-decalin. The reason for all the chair conformationz to be highly strained and trans decalin to be strain free needs to be explained.
Concept introduction:The strain in the molecule is due to a change in the C-C-C bond angle. In cyclohexane, carbon atom undergoes sp3 hybridization and the expected bond angle is 109.5o.
The formula to calculate bond angle in cyclic structure is,
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7.
(-)-Menthol is responsible for the characteristic flavor and taste of peppermint. The structure of
(-)-menthol is shown below. Use this information to answer the following question.
H3C
H.
H
H CHCH3
CH3
On the chair tempiate provided below, draw the two chair conformations that are in equilibrium for (-)-menthol
(use the correspondii.g numbers on the menthol ring above to match the same numbers on the template).
The compounds drawn should each contain a cyclohexane ring. For all three compounds draw a wedge and dash structure, Chair I, and Chair II conformations.
Formula: C9H18 with substitution 1,1- disubstituted with stereochemistry of (R,S)
Formula: C7H13Cl with substitution 1,3- disubstituted with stereochemistry of (R,R)
Formula: C7H14O with substitution 1,4- disubstituted with stereochemistry (S,S)
Draw the structures for (Z)-3-methylhex-3-ene and the two major organic products for its reaction with HBr. Be sure to show all stereoisomers using wedge and dash stereochemistry at any chirality center.
Chapter 4 Solutions
Organic Chemistry: Structure and Function
Ch. 4.1 - Prob. 4.1ECh. 4.1 - Prob. 4.3TIYCh. 4.2 - Prob. 4.4ECh. 4.2 - Prob. 4.6TIYCh. 4.3 - Prob. 4.7ECh. 4.4 - Prob. 4.8ECh. 4.4 - Prob. 4.10TIYCh. 4.4 - Prob. 4.11ECh. 4.4 - Prob. 4.12ECh. 4.4 - Prob. 4.14TIY
Ch. 4.6 - Prob. 4.15ECh. 4.7 - Prob. 4.16ECh. 4.7 - Prob. 4.17ECh. 4.7 - Prob. 4.18ECh. 4 - Prob. 21PCh. 4 - Prob. 22PCh. 4 - Prob. 23PCh. 4 - Prob. 24PCh. 4 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Prob. 27PCh. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - Prob. 40PCh. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - Prob. 43PCh. 4 - Prob. 44PCh. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Prob. 47PCh. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60P
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- 2) Draw Newman projections of all staggered conformations of (S)-butan-2-ol. Clearly mark the highest energy conformation. 3) Draw both chair conformations of (1S,3R)-1-chloro-3-isopropylcyclohexane. Clearly mark the most stable conformation, and also the conformation which enables E2 elimination.arrow_forwardDraw all possible conformations of trans-1,3-dichlorocyclobutane. Which of the conformation of trans-1,3-dichlorocyclobutane is the most stable? Explain your answer.arrow_forward11. Trans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3- methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product. (arrow_forward
- From trans-1-chloro-2-isopropylcyclohexane, only 3-isopropylcyclohexene, the less substituted alkene, is formed. Using conformational analysis, explain why this product is observed. Also, will the E2 reaction with trans-1-chloro- 2-isopropylcyclohexane or cis-1-chloro-2-isopropylcyclohexane occur faster under the same basic conditions? CH;O Na* CH3OH CI trans-1-Chloro-2 (R)-3-Isopropylcyclohexene isopropylcyclohexanearrow_forward2. Draw the two chair conformations of 3-tert-utyl-1-methylcyclohexanol and estimate the amount of strain energy in each. Which conformation is favored?arrow_forwardTrans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3-methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product.arrow_forward
- Define the degree of unsaturation ?arrow_forward(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.arrow_forwardWe saw that the energy cost of an axial methyl is 1.8 kcal/mol; therefore, we might expect cis-1,3-dimethylcyclohexane to have chair conformations with a difference in totalenergy of 3.6 kcal/mol. 1. Is the calculated energy difference in cis-1,3-dimethylcyclohexane higher or lower than expected? Propose an explanation for the difference between the expected energy difference and the calculated energy difference in cis-1,3-dimethylcyclohexane. (Limit your answer to 10 words or fewer) 2. Recall that an axial methyl is typically worth around 1.8 kcal/mol. Propose an explanation for the difference in the value above for 1-methyltetrahydropyran. (Limit your answer to 10 words or less) 3. Would you expect the difference in strain energy between the chairs of 5-methyl-1,3-dioxane to be greater than or less than that of 1-methyltetrahydropyran? Is it GREATER THAN or LESS THAN?arrow_forward
- Draw the highest and lowest energy conformations. In cases where two or three conformations are degenrate, choose only one as your answer. Use Ch2Ch3, H and Ch3 for the structure.arrow_forwardKetones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.arrow_forwardFollowing is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see Chemical Connections: A, B, AB, and O Blood Group Substances in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.arrow_forward
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