Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 16, Problem 16.29P
Name each diene and state whether the ball-and-stick model shows the diene in the
a. 
b. 
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Give the IUPAC name for each alkyne.
a. CH,CH,CH(CH,)C=CCH,CH,
d. HC=C-CH(CH2CH3)CH,CH,CH3
g.
CH3
e. CH;CH2-C-C=CH
CH,CH,CH,
b. (CH2),CHC CCH(CH3)2
c. (CH;CH2),CHC=CCH(CH,CH3)CH(CH)CH,CH3
f. CH;CH,C=CCH,C=CCH3
h.
Draw the products of each reaction. Indicate the stereochemistry of Diels–Alder products.
part i. e and h only
Chapter 16 Solutions
Organic Chemistry
Ch. 16 - Prob. 16.1PCh. 16 - Prob. 16.2PCh. 16 - Problem 16.3 Draw a second resonance structure for...Ch. 16 - Prob. 16.4PCh. 16 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 16 - Prob. 16.6PCh. 16 - Prob. 16.7PCh. 16 - Prob. 16.8PCh. 16 - Problem 16.9 Determine the hybridization of the...Ch. 16 - Problem 16.10 Draw the structure consistent with...
Ch. 16 - Problem 16.11 Neuroprotectin D1 (NPD1) is...Ch. 16 - Problem 16.12 Using hybridization, predict how the...Ch. 16 - Problem 16.13 Use resonance theory to explain why...Ch. 16 - Prob. 16.14PCh. 16 - Prob. 16.15PCh. 16 - Problem 16.16 Draw the products formed when each...Ch. 16 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 16 - Prob. 16.18PCh. 16 - Problem 16.19 Draw the product formed when each...Ch. 16 - Prob. 16.20PCh. 16 - Prob. 16.21PCh. 16 - Problem 16.22 Rank the following dienophiles in...Ch. 16 - Prob. 16.23PCh. 16 - Prob. 16.24PCh. 16 - Problem 16.25 What diene and dienophile are needed...Ch. 16 - Prob. 16.26PCh. 16 - Problem 16.27 Which compound in each pair absorbs...Ch. 16 - Prob. 16.28PCh. 16 - 16.29 Name each diene and state whether the...Ch. 16 - Prob. 16.30PCh. 16 - 16.31 Which of the following systems are...Ch. 16 - 16.32 Draw all reasonable resonance structures for...Ch. 16 - Prob. 16.33PCh. 16 - Prob. 16.34PCh. 16 - 16.35 Explain why the cyclopentadienide anion A...Ch. 16 - Prob. 16.36PCh. 16 - 16.37 Draw the structure of each compound.
a. in...Ch. 16 - Prob. 16.38PCh. 16 - 16.39 Label each pair of compounds as...Ch. 16 - Prob. 16.40PCh. 16 - 16.41 Draw the products formed when each compound...Ch. 16 - Prob. 16.42PCh. 16 - 16.43 Treatment of alkenes A and B with gives the...Ch. 16 - 16.44 Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.45PCh. 16 - 16.46 Explain, with reference to the mechanism,...Ch. 16 - Prob. 16.47PCh. 16 - Prob. 16.48PCh. 16 - Prob. 16.49PCh. 16 - Prob. 16.50PCh. 16 - Prob. 16.51PCh. 16 - Prob. 16.52PCh. 16 - 16.53 Diels–Alder reaction of a monosubstituted...Ch. 16 - Prob. 16.54PCh. 16 - 16.55 Devise a stepwise synthesis of each compound...Ch. 16 - Prob. 16.56PCh. 16 - 16.57 A transannular Diels–Alder reaction is an...Ch. 16 - Prob. 16.58PCh. 16 - Draw a stepwise mechanism for the following...Ch. 16 - Prob. 16.60PCh. 16 - Prob. 16.61PCh. 16 - Prob. 16.62PCh. 16 - Prob. 16.63PCh. 16 - Prob. 16.64PCh. 16 - 16.65 The treatment of isoprene with one...Ch. 16 - 16.66 The treatment of with forms B (molecular...Ch. 16 - Prob. 16.67PCh. 16 - Prob. 16.68PCh. 16 - Prob. 16.69PCh. 16 - Prob. 16.70PCh. 16 - Prob. 16.71PCh. 16 - Prob. 16.72PCh. 16 - Prob. 16.73PCh. 16 - Prob. 16.74PCh. 16 - Prob. 16.75P
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- Draw the products of each Diels–Alder reaction, and indicate the stereochemistry.arrow_forwardb. 1,3-cyclopentadiene reacts with 2 equivalent of HClarrow_forward2. a. b. C. Predict the products of the reactions below. Show stereochemistry, using wedges and dashes, in the products and draw both enantiomers. 1. Hg(OAc)2, H₂O 2. NaBH4 1. BH3 2. H₂O2, NaOH H₂ Pd/Carrow_forward
- Match the structure with the appropriate suffix. Match each item to a choice: H3C CH3 H3C CH2 H2C: CH3 Choices: : diyne : conjugated diene : trans alkene : cis alkene : enyne : cumulated diene : isolated diene : triynearrow_forwardWhich species in each pair is more stable?arrow_forward2) Rank the following dienes in order of increasing rate of Diels-Alder reaction with maleic anhydride. You do not need to explain your ranking. H3C. H3CO Diene A Diene B Diene Carrow_forward
- h. 3-methyl-1-butene with Hg(OAC)2 and CH3OH, followed later by NaBH4 CH3 H2C=CH-CH-CH3 Major Product(s) of h. Stereochemistry of the product described in h. (Circle one) а. R b. S С. Е d. Z e. a mixture of E and Z f. erythro g. threo h. a racemic (50/50) mixture i. all 4 products (a set of erythro and a set of threo) j. no stereochemistryarrow_forwardg. cis-3-methylpent-2-ene with BH3, H2O2, and OH CH3 H3C- CH =C -CH2-CH3 Major Product(s) of g. Stereochemistry of the product described in g. (Circle one) а. R b. S С. Е d. Z e. a mixture of E and Z f. erythro g. threo h. a racemic (50/50) mixture i. all 4 products (a set of erythro and a set of threo) j. no stereochemistryarrow_forwardDraw the products formed when ethylene oxide is treated with each reagent. a. HBr b. H2O(H2SO4) c. [1] CH3CH2O; [2] H2O d. [1] HC ≡ C−; [2] H2O e. [1] −OH; [2] H2O f. [1] CH3S−; [2] H2Oarrow_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_forwardRank the following dienes in order of increasing reactivity in a Diels-Alder reaction.arrow_forwardQ.2 charrow_forward
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