10 Ch06 - 184 CHAPTER 6 The Reactions of Alkynes An...

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184 CHAPTER 6 The Reactions of Alkynes • An Introduction to Multistep Synthesis Important Terms acetylide ion the conjugate base of a terminal alkyne RC C aldehyde a compound with a carbonyl group that is bonded to an alkyl group and to a hydrogen (or bonded to two hydrogens). O C R H or O C H H alkylation reaction a reaction that adds an alkyl group to a reactant. alkyne a hydrocarbon that contains a triple bond. carbonyl group a carbon doubly bonded to an oxygen. O C enol an α , β -unsaturated alcohol. OH C geminal dihalide a compound with two halogen atoms bonded to the same carbon. internal alkyne an alkyne with its triple bond not at the end of the carbon chain. keto-enol tautomers a ketone and its isomeric , -unsaturated alcohol. O CR RCH 2 keto enol RCH CR OH ketone a compound with a carbonyl group that is bonded to two alkyl groups. O C R R π -complex a complex formed between an electrophile and a triple bond. polymer a large molecule made by linking up many small molecules called monomers. radical anion a species with a negative charge and an unpaired electron.
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Chapter 6 185 retrosynthetic analysis working backward (on paper) from a target molecule to available starting or materials. retrosynthesis tautomerization interconversion of tautomers. tautomers isomers that are in rapid equilibrium. The keto and enol tautomers differ in the location of a double bond and a hydrogen. terminal alkyne an alkyne with its triple bond at the end of the carbon chain. vinylic cation a compound with a positive charge on a vinylic carbon. vinylic radical a compound with an unpaired electron on a vinylic carbon.
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186 Chapter 6 Solutions to Problems 1. The molecular formula of a noncyclic hydrocarbon with 14 carbons and no π bonds is 14 30 2 +2 CH ( CH ) nn . Because a compound has two fewer hydrogens for every ring and bond, a compound with one ring and 4 bonds (2 triple bonds) would have 10 fewer hydrogens than the 2+ 2 formula. Thus, the molecular formula is 14 20 . 2. a. 22 23 ClCH CH C CCH CH c. CH 3 CHC CH 3 CH e. HC CCH 2 CCH 3 CH 3 CH 3 b. d. 2 HC CCH Cl f. 33 CH C CCH 3. To answer this question, you need to have the information in Section 6.2. a. 1-bromo-1,3-pentadiene b. 1-hepten-5-yne c. 4-hepten-1-yne 4. HC CCH 2 CH 2 CH 2 CH 3 CH 3 C CCH 2 CH 2 CH 3 CH 3 CH 2 CC C H 2 CH 3 1-hexyne butylacetylene 2-hexyne methylpropylacetylene 3-hexyne diethylacetylene CH 3 CH 2 CHC CH CH 3 CHCH 2 H CH 3 CHC CCH 3 3-methyl-1-pentyne sec -butylacetylene 4-methyl-1-pentyne isobutylacetylene CH 3 CH 3 CH 3 4-methyl-2-pentyne isopropylmethylacetylene CH 3 CC 3,3-dimethyl-1-butyne tert -butylacetylene CH CH 3 CH 3 5. a. 5-bromo-2-pentyne c. 1-methoxy-2-pentyne b. 6-bromo-2-chloro-4-octyne d. 3-ethyl-1-hexyne 6. a. 1-hepten-4-yne d. 3-butyn-1-ol b. 4-methyl-1,4-hexadiene e. 1,3,5-heptatriene c. 5-vinyl-5-octen-1-yne f. 2,4-dimethyl-4-hexen-1-ol 7. pentane 1-pentene 1-pentyne
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Chapter 6 187 8. a. sp 2 sp 2 d. sp sp 3 g. sp 2 sp 3 b. sp 2 sp 3 e. sp sp h. sp sp 3 c. sp sp 2 f. sp 2 sp 2 i. sp 2
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